Transition-Metal-Catalyzed
Carbon-Carbon Bond Formation via Carbon-Hydrogen
Bond Cleavage

Fumitoshi Kakiuchi; Takuya Kochi

doi:10.1055/s-2008-1067256

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2008(19): 3013-3039
DOI: 10.1055/s-2008-1067256

REVIEW

Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage

Fumitoshi Kakiuchi*, Takuya Kochi
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan
Fax: +81(45)5661591; e-Mail: kakiuchi@chem.keio.ac.jp;

Further Information

Publication History

Received 29 February 2008
Publication Date:
05 September 2008 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Catalytic functionalization of unreactive C-H bond has become one of the most attractive research subjects in modern organic chemistry. To date, a variety of catalytic reactions involving C-H bond cleavage have been reported. In this review, we briefly survey the reported research with respect to efficient and selective transition-metal-catalyzed C-C bond formation via C-H bond cleavage.

1 Introduction

2 Addition of C-H Bonds to C-C Multiple Bonds

3 Alkenylation of C-H Bonds via Substitution Reactions

4 Carbonylation and Acylation of C-H Bonds Using Carbon Monoxide

5 Arylation of C-H Bonds

6 Sequential Coupling of Aryl Halides with Alkyl Halides Using Norbornene as a Mediator

7 Conversion of C-H Bonds into C-C Bonds via 1,4- and 1,5-Transition-Metal Migrations

8 Addition of C-H Bonds to Polar C=X Bonds

9 Conclusions

Key words

C-H bond cleavage - alkylation - alkenylation - arylation - transition-metal catalysts

References

1 Blanksby SJ. Ellison GB. Acc. Chem. Res. 2003, 36: 255

Crossref PubMed Google Scholar
2 Kleiman JP. Dubeck M. J. Am. Chem. Soc. 1963, 85: 1544

Crossref Google Scholar
3a Chatt J. Watson HW. J. Chem. Soc. 1962, 2545

Google Scholar
3b Chatt J. Davidson JM. J. Chem. Soc. 1965, 843

Google Scholar
4a Bergman RG. Science 1984, 223: 902

Google Scholar
4b Crabtree RH. Chem. Rev. 1985, 85: 245

Google Scholar
4c Shilov AE. Shul’pin GB. Chem. Rev. 1997, 97: 2879

Google Scholar
4d Labinger JA. Bercaw JE. Nature 2002, 417: 507

Google Scholar
4e Bergman RG. Nature 2007, 446: 391

Google Scholar
5 Fujiwara Y. Moritani I. Danno S. Asano R. Teranishi S. J. Am. Chem. Soc. 1969, 91: 7166

Google Scholar
6 Hong P. Yamazaki H. Sonogashira K. Hagihara N. Chem. Lett. 1978, 7: 535

Crossref Google Scholar
7 Lewis LN. Smith JF. J. Am. Chem. Soc. 1986, 108: 2728

Crossref Google Scholar
8a Murai S. Kakiuchi F. Sekine S. Tanaka Y. Kamatani A. Sonoda M. Chatani N. Nature 1993, 366: 529

Google Scholar
8b Murai S. Kakiuchi F. Sekine S. Tanaka Y. Kamatani A. Sonoda M. Chatani N. Pure Appl. Chem. 1994, 66: 1527

Google Scholar
8c Kakiuchi F. Sekine S. Tanaka Y. Kamatani A. Sonoda M. Chatani N. Murai S. Bull. Chem. Soc. Jpn. 1995, 68: 62

Google Scholar
8d Sonoda M. Kakiuchi F. Chatani N. Murai S. J. Organomet. Chem. 1995, 504: 151

Google Scholar
8e Sonoda M. Kakiuchi F. Chatani N. Murai S. Bull. Chem. Soc. Jpn. 1997, 70: 3117

Google Scholar
8f Kakiuchi F. Murai S. Org. Synth. 2003, 80: 104

Google Scholar
9a Kakiuchi F. Murai S. Top. Organomet. Chem. 1999, 3: 47

Google Scholar
9b Dyker G. Angew. Chem. Int. Ed. 1999, 38: 1698

Google Scholar
9c Ritleng V. Sirlin C. Pfeffer M. Chem. Rev. 2002, 102: 1731

Google Scholar
9d Kakiuchi F. Chatani N. Adv. Synth. Catal. 2003, 345: 1077

Google Scholar
9e Park YJ. Jun C.-H. Bull. Korean Chem. Soc. 2005, 26: 871

Google Scholar
9f Godula K. Sames D. Science 2006, 312: 67

Google Scholar
10a Jordan RF. Taylor DF. J. Am. Chem. Soc. 1989, 111: 778

Google Scholar
10b Rodewald S. Jordan RF. J. Am. Chem. Soc. 1994, 116: 4491

Google Scholar
11a Guo H. Tapsak MA. Weber WP. Macromolecules 1995, 28: 4714

Google Scholar
11b Lu P. Paulasaari J. Jin K. Bau R. Weber WP. Organometallics 1998, 17: 584

Google Scholar
11c Gupta SK. Weber WP. Macromolecules 2000, 33: 108

Google Scholar
12 Grigg R. Savic V. Tetrahedron Lett. 1997, 38: 5737

Crossref Google Scholar
13a Harris PWR. Woodgate PD. J. Organomet. Chem. 1996, 506: 339

Google Scholar
13b Harris PWR. Woodgate PD. J. Organomet. Chem. 1997, 530: 211

Google Scholar
13c Harris PWR. Woodgate PD. Tetrahedron 2000, 56: 4001

Google Scholar
14a Grellier M. Vendier L. Chaudret B. Albinati A. Rizzato S. Mason S. Sabo-Etienne S. J. Am. Chem. Soc. 2005, 127: 17592

Google Scholar
14b Guari Y. Castellanos A. Sabo-Etienne S. Chaudret B. J. Mol. Catal. A: Chem. 2004, 212: 77

Google Scholar
15a Busch S. Leitner W. Chem. Commun. 1999, 2305

Google Scholar
15b Busch S. Leitner W. Adv. Synth. Catal. 2001, 343: 192

Google Scholar
16 Martinez R. Chevalier R. Darses S. Genet J.-P. Angew. Chem. Int. Ed. 2006, 45: 8232

Crossref PubMed Google Scholar
17a Matsubara T. Koga N. Musaev DG. Morokuma K. J. Am. Chem. Soc. 1998, 120: 12692

Google Scholar
17b Matsubara T. Koga N. Musaev DG. Morokuma K. Organometallics 2000, 19: 2318

Google Scholar
18 Lenges CP. Brookhart M. J. Am. Chem. Soc. 1999, 121: 6616

Crossref Google Scholar
19 Jazzar RFR. Mahon MF. Whittlesey MK. Organometallics 2001, 20: 3745

Crossref Google Scholar
20 Drouin SD. Amoroso D. Yap GPA. Fogg DE. Organometallics 2002, 21: 1042

Crossref Google Scholar
21a Sonoda M. Kakiuchi F. Kamatani A. Chatani N. Murai S. Chem. Lett. 1996, 109

Google Scholar
21b Kakiuchi F. Ohtaki H. Sonoda M. Chatani N. Murai S. Chem. Lett. 2001, 918

Google Scholar
22 Aufdenblatten R. Diezi S. Togni A. Monatsh. Chem. 2000, 131: 1345

Crossref Google Scholar
23 Tsuji J. Ohno K. Tetrahedron Lett. 1965, 3969

Crossref Google Scholar
24a Bosnich B. Acc. Chem. Res. 1998, 31: 667

Google Scholar
24b Jun C.-H. Jo E.-A. Park J.-W. Eur. J. Org. Chem. 2007, 1869

Google Scholar
25 Kakiuchi F. Sato T. Igi K. Chatani N. Murai S. Chem. Lett. 2001, 386

Crossref Google Scholar
26a Kakiuchi F. Yamauchi M. Chatani N. Murai S. Chem. Lett. 1996, 111

Google Scholar
26b Kakiuchi F. Sato T. Tsujimoto T. Yamauchi M. Chatani N. Murai S. Chem. Lett. 1998, 1053

Google Scholar
27a Lim Y.-G. Han J.-S. Yang S.-S. Chun JH. Tetrahedron Lett. 2001, 42: 4853

Google Scholar
27b Lim Y.-G. Koo BT. Tetrahedron Lett. 2005, 46: 7997

Google Scholar
28a Jun C.-H. Hong J.-B. Kim Y.-H. Chung K.-Y. Angew. Chem. Int. Ed. 2000, 39: 3440

Google Scholar
28b Lim S.-G. Ahn J.-A. Jun C.-H. Org. Lett. 2004, 6: 4687

Google Scholar
28c Yoon JH. Park YJ. Lee JH. Yoo J. Jun C.-H. Org. Lett. 2005, 7: 2889

Google Scholar
28d Jo E.-A. Cho E.-G. Jun C.-H. Synlett 2007, 1059

Google Scholar
29 Kakiuchi F. Tsujimoto T. Sonoda M. Chatani N. Murai S. Synlett 2001, 948

Article in Thieme Connect Google Scholar
30a Lim Y.-G. Kim YH. Kang J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267

Google Scholar
30b Lim Y.-G. Kang J.-B. Kim YH. J. Chem. Soc., Perkin Trans. 1 1996, 2201

Google Scholar
31 Kakiuchi F. Le Gendre P. Yamada A. Ohtaki H. Murai S. Tetrahedron: Asymmetry 2000, 11: 2647

Crossref Google Scholar
32 Kakiuchi F. Sato T. Yamauchi M. Chatani N. Murai S. Chem. Lett. 1999, 19

Crossref Google Scholar
33 Kakiuchi F. Sonoda M. Tsujimoto T. Chatani N. Murai S. Chem. Lett. 1999, 1083

Crossref Google Scholar
34a Tan KL. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2002, 124: 3202

Google Scholar
34b Tan KL. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2002, 124: 13964

Google Scholar
34c Tan KL. Park S. Ellman JA. Bergman RG. J. Org. Chem. 2004, 69: 7329

Google Scholar
34d Wiedemann SH. Bergman RG. Ellman JA. Org. Lett. 2004, 6: 1685

Google Scholar
34e Wiedemann SH. Ellman JA. Bergman RG. J. Org. Chem. 2006, 71: 1969

Google Scholar
34f Wiedemann SH. Lewis JC. Ellman JA. Bergman RG. J. Am. Chem. Soc. 2006, 128: 2452

Google Scholar
34g Lewis JC. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2007, 129: 5332

Google Scholar
35a Matsumoto T. Taube DJ. Periana RA. Taube H. Yoshida H. J. Am. Chem. Soc. 2000, 122: 7414

Google Scholar
35b Oxgaard J. Muller RP. Goddard WA. J. Am. Chem. Soc. 2004, 126: 352

Google Scholar
35c Oxgaard J. Periana RA. Goddard WA. J. Am. Chem. Soc. 2004, 126: 11658

Google Scholar
35d Bhalla G. Liu XY. Oxgaard J. Goddard WA. J. Am. Chem. Soc. 2005, 127: 11372

Google Scholar
35e Bhalla G. Oxgaard J. Goddard WA. Organometallics 2005, 24: 3229

Google Scholar
36a Lail M. Bell CM. Conner D. Cundari TR. Gunnoe TB. Petersen JL. Organometallics 2004, 23: 5007

Google Scholar
36b Foley NA. Lail M. Lee JP. Gunnoe TB. Cundari TR. Petersen JL. J. Am. Chem. Soc. 2007, 129: 6765

Google Scholar
36c DeYonker NJ. Foley NA. Cundari TR. Gunnoe TB. Petersen JL. Organometallics 2007, 26: 6604

Google Scholar
36d Gunnoe TB. Eur. J. Inorg. Chem. 2007, 1185

Google Scholar
37 Trost BM. Imi K. Davies IW. J. Am. Chem. Soc. 1995, 117: 5371

Crossref Google Scholar
38a Kakiuchi F. Tanaka Y. Sato T. Chatani N. Murai S. Chem. Lett. 1995, 679

Google Scholar
38b Sato T. Kakiuchi F. Chatani N. Murai S. Chem. Lett. 1998, 893

Google Scholar
39a Lim Y.-G. Kang J.-B. Kim YH. Chem. Commun. 1996, 585

Google Scholar
39b Lim Y.-G. Kang J.-B. Kim YH. J. Chem. Soc., Perkin Trans. 1 1998, 699

Google Scholar
39c Lim Y.-G. Kang J.-B. Koo BT. Tetrahedron Lett. 1999, 40: 7691

Google Scholar
39d Lim Y.-G. Kang J.-B. Lee K. Kim YH. Heteroat. Chem. 2002, 13: 346

Google Scholar
40 Diamond SE. Szalkiewicz A. Mares F. J. Am. Chem. Soc. 1979, 101: 490

Crossref Google Scholar
41 Beller M. Thiel OR. Trauthwein H. Hartung CG. Chem. Eur. J. 2000, 6: 2513

Google Scholar
42a Cho CS. Lim HK. Shim SC. Kim TJ. Chi H.-J. Chem. Commun. 1998, 995

Google Scholar
42b Cho CS. Kim JS. Oh BH. Kim T.-J. Shim SC. Yoon NS. Tetrahedron 2000, 56: 7747

Google Scholar
43a Jacob J. Cavalier CM. Jones WD. Godleski SA. Valent RR. J. Mol. Catal. A: Chem. 2002, 182-183: 565

Google Scholar
43b Li L. Jones WD. J. Am. Chem. Soc. 2007, 129: 10707

Google Scholar
44 Nugent WA. Ovenall DW. Holmes SJ. Organometallics 1983, 2: 161

Crossref Google Scholar
45 Jun C.-H. Hwang D.-C. Na S.-J. Chem. Commun. 1998, 1405

Crossref Google Scholar
46 Chatani N. Asaumi T. Yorimitsu S. Ikeda T. Kakiuchi F. Murai S. J. Am. Chem. Soc. 2001, 123: 10935

Crossref PubMed Google Scholar
47a Fujii N. Kakiuchi F. Chatani N. Murai S. Chem. Lett. 1996, 939

Google Scholar
47b Fujii N. Kakiuchi F. Yamada A. Chatani N. Murai S. Chem. Lett. 1997, 425

Google Scholar
47c Fujii N. Kakiuchi F. Yamada A. Chatani N. Murai S. Bull. Chem. Soc. Jpn. 1998, 71: 285

Google Scholar
48a Tan KL. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2001, 123: 2685

Google Scholar
48b Thalji RK. Ahrendt KA. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2001, 123: 9692

Google Scholar
48c Thalji RK. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2004, 126: 7192

Google Scholar
48d Rech JC. Yato M. Duckett D. Ember B. LoGrasso PV. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2007, 129: 490

Google Scholar
49 DeBoef B. Pastine SJ. Sames D. J. Am. Chem. Soc. 2004, 126: 6556

Google Scholar
50a Hong P. Cho B.-R. Yamazaki H. Chem. Lett. 1979, 9: 339

Google Scholar
50b Hong P. Cho B.-R. Yamazaki H. Chem. Lett. 1980, 10: 507

Google Scholar
50c Yamazaki H. Hong P. J. Mol. Catal. 1983, 21: 133

Google Scholar
51a Halbritter G. Knoch F. Wolski A. Kisch H. Angew. Chem., Int. Ed. Engl. 1994, 33: 1603

Google Scholar
51b Dürr U. Kisch H. Synlett 1997, 1335

Google Scholar
52a Kakiuchi F. Yamamoto Y. Chatani N. Murai S. Chem. Lett. 1995, 681

Google Scholar
52b Kakiuchi F. Uetsuhara T. Tanaka Y. Chatani N. Murai S. J. Mol. Catal. A: Chem. 2002, 511: 182

Google Scholar
53 Harris PWR. Rickard CEF. Woodgate PD. J. Organomet. Chem. 1999, 589: 168

Google Scholar
54 Londergan TM. You Y. Thompson ME. Weber WP. Macromolecules 1998, 31: 2784

Crossref Google Scholar
55 Satoh T. Nishinaka Y. Miura M. Nomura M. Chem. Lett. 1999, 615

Crossref Google Scholar
56 Lim S.-G. Lee JH. Moon CW. Hong J.-B. Jun C.-H. Org. Lett. 2003, 5: 2759

Crossref PubMed Google Scholar
57 Lim Y.-G. Lee K.-H. Koo BT. Kang J.-B. Tetrahedron Lett. 2001, 42: 7609

Crossref Google Scholar
58a Kuninobu Y. Kawata A. Takai K. J. Am. Chem. Soc. 2005, 127: 13498

Google Scholar
58b Kuninobu Y. Tokunaga Y. Kawata A. Takai K. J. Am. Chem. Soc. 2006, 128: 202

Google Scholar
59a Ueura K. Satoh T. Miura M. Org. Lett. 2007, 9: 1407

Google Scholar
59b Ueura K. Satoh T. Miura M. J. Org. Chem. 2007, 72: 5362

Google Scholar
60a Tsukada N. Mitsuboshi T. Setoguchi H. Inoue Y. J. Am. Chem. Soc. 2003, 125: 12102

Google Scholar
60b Tsukada N. Murata K. Inoue Y. Tetrahedron Lett. 2005, 46: 7515

Google Scholar
61 Nakao Y. Yada A. Ebata S. Hiyama T. J. Am. Chem. Soc. 2007, 129: 2428

Crossref PubMed Google Scholar
62a Sakaguchi S. Kubo T. Ishii Y. Angew. Chem. Int. Ed. 2001, 40: 2534

Google Scholar
62b Ishii Y. Sakaguchi S. Bull. Chem. Soc. Jpn. 2004, 77: 909

Google Scholar
63a Tunge JA. Foresee LN. Organometallics 2005, 24: 6440

Google Scholar
63b Fürstner A. Davies PW. Angew. Chem. Int. Ed. 2007, 46: 3410

Google Scholar
64a Hong P. Yamazaki H. Chem. Lett. 1979, 1335

Google Scholar
64b Lin Y. Ma D. Lu X. Tetrahedron Lett. 1987, 28: 3249

Google Scholar
65 Tsuji J. Nagashima H. Tetrahedron 1984, 40: 2699

Crossref Google Scholar
66a Yokota T. Tani M. Sakaguchi S. Ishii Y. J. Am. Chem. Soc. 2003, 125: 1476

Google Scholar
66b Tani M. Sakaguchi S. Ishii Y. J. Org. Chem. 2004, 69: 1221

Google Scholar
66c Yamada T. Sakaguchi S. Ishii Y. J. Org. Chem. 2005, 70: 5471

Google Scholar
67 Dams M. De Vos DE. Celen S. Jacobs PA. Angew. Chem. Int. Ed. 2003, 42: 3512

Crossref PubMed Google Scholar
68a Matsumoto T. Yoshida H. Chem. Lett. 2000, 1064

Google Scholar
68b Matsumoto T. Periana RA. Taube DJ. Yoshida H. J. Catal. 2002, 206: 272

Google Scholar
68c Weissman H. Song X. Milstein D. J. Am. Chem. Soc. 2001, 123: 337

Google Scholar
69 Mikami K. Hatano M. Terada M. Chem. Lett. 1999, 55

Crossref Google Scholar
70 Miura M. Tsuda T. Satoh T. Nomura M. Chem. Lett. 1997, 1103

Crossref Google Scholar
71 Miura M. Tsuda T. Satoh T. Pivsa-Art S. Nomura M. J. Org. Chem. 1998, 63: 5211

Crossref Google Scholar
72a Boele MDK. van Strijdonck GPF. de Vries AHM. Kamer PCJ. de Vries JD. van Leeuwen PWNM. J. Am. Chem. Soc. 2002, 124: 1586

Google Scholar
72b Boele MDK. van Strijdonck GPF. de Vries AHM. Kamer PCJ. de Vries JG. van Leeuwen PWNM. J. Am. Chem. Soc. 2005, 127: 4156

Google Scholar
73 Cai G. Fu Y. Li Y. Wan X. Shi Z. J. Am. Chem. Soc. 2007, 129: 7666

Crossref PubMed Google Scholar
74a Grimster NP. Gauntlett C. Godfrey CRA. Gaunt MJ. Angew. Chem. Int. Ed. 2005, 44: 3125

Google Scholar
74b Beck EM. Grimster NP. Hatley R. Gaunt MJ. J. Am. Chem. Soc. 2006, 128: 2528

Google Scholar
75a Oi S. Fukita S. Hirata N. Watanuki N. Miyano S. Inoue Y. Org. Lett. 2001, 3: 2579

Google Scholar
75b Oi S. Ogino Y. Fukita S. Inoue Y. Org. Lett. 2002, 4: 1783

Google Scholar
75c Oi S. Aizawa E. Ogino Y. Inoue Y. J. Org. Chem. 2005, 70: 3113

Google Scholar
76 Zaitsev VG. Daugulis O. J. Am. Chem. Soc. 2005, 127: 4156

Crossref PubMed Google Scholar
77 Matsuura Y. Tamura M. Kochi T. Sato M. Chatani N. Kakiuchi F. J. Am. Chem. Soc. 2007, 129: 9858

Crossref PubMed Google Scholar
78 Ueno S. Chatani N. Kakiuchi F. J. Org. Chem. 2007, 72: 3600

Crossref PubMed Google Scholar
79a Fisher BJ. Eisenberg R. Organometallics 1983, 2: 764

Google Scholar
79b Kunin AJ. Eisenberg R. J. Am. Chem. Soc. 1986, 108: 535

Google Scholar
79c Gordon EM. Eisenberg R. J. Mol. Catal. 1988, 45: 57

Google Scholar
79d Kunin AJ. Eisenberg R. Organometallics 1988, 7: 2124

Google Scholar
80a Sakakura T. Tanaka M. Chem. Lett. 1987, 249

Google Scholar
80b Sakakura T. Tanaka M. J. Chem. Soc., Chem. Commun. 1987, 758

Google Scholar
80c Sakakura T. Tanaka M. Chem. Lett. 1987, 1113

Google Scholar
80d Sakakura T. Sodeyama T. Sasaki K. Wada K. Tanaka M. J. Am. Chem. Soc. 1990, 112: 7221

Google Scholar
80e Tanaka M. Sakakura T. Pure Appl. Chem. 1990, 62: 1147

Google Scholar
81 Boyd SE. Field LD. Partridge MG. J. Am. Chem. Soc. 1994, 116: 9492

Crossref Google Scholar
82 Rosini GP. Boese WT. Goldman AS. J. Am. Chem. Soc. 1994, 116: 9498

Crossref Google Scholar
83 Bridgewater JS. Lee B. Bernhard S. Schoonover JR. Ford PC. Organometallics 1997, 16: 5592

Crossref Google Scholar
84 Koga N. Morokuma K. J. Phys. Chem. 1990, 94: 5454

Crossref Google Scholar
85a Margl P. Ziegler T. Blöchl PE. J. Am. Chem. Soc. 1995, 117: 12625

Google Scholar
85b Margl P. Ziegler T. Blöchl PE. J. Am. Chem. Soc. 1996, 118: 5412

Google Scholar
86a Jones WD. Kosar WP. J. Am. Chem. Soc. 1986, 108: 5640

Google Scholar
86b Hsu GC. Kosar WP. Jones WD. Organometallics 1994, 13: 385

Google Scholar
87a Jones WD. Foster GP. Putinas JM. J. Am. Chem. Soc. 1987, 109: 5047

Google Scholar
87b Jones WD. Hessell ET. Organometallics 1990, 9: 718

Google Scholar
88 Tanaka M. Sakakura T. Tokunaga Y. Sodeyama T. Chem. Lett. 1987, 2373

Crossref Google Scholar
89 Moore EJ. Pretzer WR. O’Connell TJ. Harris J. LaBounty L. Chou L. Grimmer SC. J. Am. Chem. Soc. 1992, 114: 5888

Crossref Google Scholar
90a Chatani N. Fukuyama T. Kakiuchi F. Murai S. J. Am. Chem. Soc. 1996, 118: 493

Google Scholar
90b Chatani N. Fukuyama T. Tatamidani H. Kakiuchi F. Murai S. J. Org. Chem. 2000, 65: 4039

Google Scholar
91 Fukuyama T. Chatani N. Tatsumi J. Kakiuchi F. Murai S. J. Am. Chem. Soc. 1998, 120: 11522

Crossref Google Scholar
92a Chatani N. Ie Y. Kakiuchi F. Murai S. J. Org. Chem. 1997, 62: 2604

Google Scholar
92b Chatani N. Uemura T. Asaumi T. Ie Y. Kakiuchi F. Murai S. Can. J. Chem. 2005, 83: 755

Google Scholar
92c Imoto S. Uemura T. Kakiuchi F. Chatani N. Synlett 2007, 170

Google Scholar
93 Ie Y. Chatani N. Ogo T. Marshall DR. Fukuyama T. Kakiuchi F. Murai S. J. Org. Chem. 2000, 65: 1475

Google Scholar
94 Fukuyama T. Chatani N. Kakiuchi F. Murai S. J. Org. Chem. 1997, 62: 5647

Crossref Google Scholar
95 Chatani N. Yorimitsu S. Asaumi T. Kakiuchi F. Murai S. J. Org. Chem. 2002, 67: 7557

Crossref PubMed Google Scholar
96 Szewczyk JW. Zuckerman RL. Bergman RG. Ellman JA. Angew. Chem. Int. Ed. 2001, 40: 216

Crossref PubMed Google Scholar
97 Chatani N. Asaumi T. Ikeda T. Yorimitsu S. Ishii Y. Kakiuchi F. Murai S. J. Am. Chem. Soc. 2000, 122: 12882

Crossref Google Scholar
98 Ishii Y. Chatani N. Kakiuchi F. Murai S. Organometallics 1997, 16: 3615

Crossref Google Scholar
99 Ishii Y. Chatani N. Kakiuchi F. Murai S. Tetrahedron Lett. 1997, 38: 7565

Crossref Google Scholar
100a Satoh T. Miura M. Nomura M. J. Organomet. Chem. 2002, 653: 161

Google Scholar
100b Catellani M. Synlett 2003, 298

Google Scholar
100c Campeau L.-C. Fagnou K. Chem. Commun. 2006, 1253

Google Scholar
100d Daugulis O. Zaitsev VG. Shabashov D. Pham Q.-N. Lazareva A. Synlett 2006, 3382

Google Scholar
100e Satoh T. Miura M. Chem. Lett. 2007, 36: 200

Google Scholar
100f Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 174

Google Scholar
100g Ackermann L. Synlett 2007, 507

Google Scholar
100h Pascual S. de Mendoza P. Echavarren AM. Org. Biomol. Chem. 2007, 5: 2727

Google Scholar
101 Nakamura N. Tajima Y. Sakai K. Heterocycles 1982, 17: 235

Crossref Google Scholar
102a Catellani M. Chiusoli GP. J. Organomet. Chem. 1985, 286: 13

Google Scholar
102b Catellani M. Chiusoli GP. Castagnoli C. J. Organomet. Chem. 1991, 407: C30

Google Scholar
103a Reiser O. Weber M. de Meijere A. Angew. Chem., Int. Ed. Engl. 1989, 28: 1037

Google Scholar
103b Albrecht K. Reiser O. Weber M. Knieriem B. de Meijere A. Tetrahedron 1994, 50: 383

Google Scholar
104a Satoh T. Kawamura Y. Miura M. Nomura M. Angew. Chem., Int. Ed. Engl. 1997, 36: 1740

Google Scholar
104b Satoh T. Inoh J.-i. Kawamura Y. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 2239

Google Scholar
105 Kawamura Y. Satoh T. Miura M. Nomura M. Chem. Lett. 1998, 961

Crossref Google Scholar
106a Bedford RB. Coles SJ. Hursthouse MB. Limmert ME. Angew. Chem. Int. Ed. 2003, 42: 112

Google Scholar
106b Bedford RB. Limmert ME. J. Org. Chem. 2003, 68: 8669

Google Scholar
107 Oi S. Watanabe S.-i. Fukita S. Inoue Y. Tetrahedron Lett. 2003, 44: 8665

Crossref Google Scholar
108 Lewis JC. Wu J. Bergman RG. Ellman JA. Organometallics 2005, 24: 5737

Crossref Google Scholar
109 Satoh T. Kametani Y. Terao Y. Miura M. Nomura M. Tetrahedron Lett. 1999, 40: 5345

Google Scholar
110 Kametani Y. Satoh T. Miura M. Nomura M. Tetrahedron Lett. 2000, 41: 2655

Crossref Google Scholar
111 Terao Y. Kametani Y. Wakui H. Satoh T. Miura M. Nomura M. Tetrahedron 2001, 57: 5967

Crossref Google Scholar
112a Shabashov D. Daugulis O. Org. Lett. 2006, 8: 4947

Google Scholar
112b Shabashov D. Daugulis O. J. Org. Chem. 2007, 72: 7720 ; and references cited therein

Google Scholar
113 Okazawa T. Satoh T. Miura M. Nomura M. J. Am. Chem. Soc. 2002, 124: 5286

Crossref PubMed Google Scholar
114 Glover B. Harvey KA. Liu B. Sharp MJ. Tymoschenko MF. Org. Lett. 2003, 5: 301

Crossref PubMed Google Scholar
115 Ackermann L. Org. Lett. 2005, 7: 3123

Crossref PubMed Google Scholar
116 Ackermann L. Althammer A. Born R. Angew. Chem. Int. Ed. 2006, 45: 2619

Crossref PubMed Google Scholar
117a Lafrance M. Rowley CN. Woo TK. Fagnou K. J. Am. Chem. Soc. 2006, 128: 8754

Google Scholar
117b Lafrance M. Fagnou K. J. Am. Chem. Soc. 2006, 128: 16496

Google Scholar
117c Fujita K.-i. Nonogawa M. Yamaguchi R. Chem. Commun. 2006, 1926

Google Scholar
118a Campeau L.-C. Rousseaux S. Fagnou K. J. Am. Chem. Soc. 2005, 127: 18020

Google Scholar
118b Leclerc J.-P. Fagnou K. Angew. Chem. Int. Ed. 2006, 45: 7781

Google Scholar
119 Miura M. Pivsa-Art S. Dyker G. Heiermann J. Satoh T. Nomura M. Chem. Commun. 1998, 1889

Crossref Google Scholar
120a Kalyani D. Deprez NR. Desai LV. Sanford MS. J. Am. Chem. Soc. 2005, 127: 7330

Google Scholar
120b Daugulis O. Zaitsev VG. Angew. Chem. Int. Ed. 2005, 44: 4046

Google Scholar
120c Deprez NR. Kalyani D. Krause A. Sanford MS. J. Am. Chem. Soc. 2006, 128: 4972

Google Scholar
121 Oi S. Sakai K. Inoue Y. Org. Lett. 2005, 7: 4009

Crossref Google Scholar
122a Dyker G. Angew. Chem., Int. Ed. Engl. 1992, 31: 1023

Google Scholar
122b Dyker G. Angew. Chem., Int. Ed. Engl. 1994, 33: 103

Google Scholar
123 Inoh J.-I. Satoh T. Pivsa-Art S. Miura M. Nomura M. Tetrahedron Lett. 1998, 39: 4673

Crossref Google Scholar
124a Shabashov D. Daugulis O. Org. Lett. 2005, 7: 3657

Google Scholar
124b Zaitsev VG. Shabashov D. Daugulis O. J. Am. Chem. Soc. 2005, 127: 13154

Google Scholar
125a Akita Y. Itagaki Y. Takizawa S. Ohta A. Chem. Pharm. Bull. 1989, 37: 1477

Google Scholar
125b Aoyagi Y. Inoue A. Koizumi I. Hashimoto R. Tokunaga K. Gohma K. Komatsu J. Sekine K. Miyafuji A. Kunoh J. Honma R. Akita Y. Ohta A. Heterocycles 1992, 33: 257

Google Scholar
126 Pivsa-Art S. Satoh T. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467

Crossref Google Scholar
127 Lavenot L. Gozzi C. Ilg K. Orlova I. Penalva V. Lemaire M. J. Organomet. Chem. 1998, 567: 49

Crossref Google Scholar
128 Masui K. Mori A. Okano K. Takamura K. Kinoshita M. Ikeda T. Org. Lett. 2004, 6: 2011

Crossref PubMed Google Scholar
129 Yokooji A. Satoh T. Miura M. Nomura M. Tetrahedron 2004, 60: 6757

Crossref Google Scholar
130 Kobayashi K. Sugie A. Takahashi M. Masui K. Mori A. Org. Lett. 2005, 7: 5083

Google Scholar
131 McClure MS. Glover B. McSorley E. Millar A. Osterhout MH. Roschangar F. Org. Lett. 2001, 3: 1677

Crossref PubMed Google Scholar
132 Nakano M. Satoh T. Miura M. J. Org. Chem. 2006, 71: 8309

Crossref PubMed Google Scholar
133 Yanagisawa S. Sudo T. Noyori R. Itami K. J. Am. Chem. Soc. 2006, 128: 11748

Crossref PubMed Google Scholar
134 Park C.-H. Ryabova V. Seregin IV. Sromek AW. Gevorgyan V. Org. Lett. 2004, 6: 1159

Crossref PubMed Google Scholar
135a Mori A. Sekiguchi A. Masui K. Shimada T. Horie M. Osakada K. Kawamoto M. Ikeda T. J. Am. Chem. Soc. 2003, 125: 1700

Google Scholar
135b Yokooji A. Okazawa T. Satoh T. Miura M. Nomura M. Tetrahedron 2003, 59: 5685

Google Scholar
136a Bellina F. Cauteruccio S. Mannina L. Rossi R. Viel S. J. Org. Chem. 2005, 70: 3997

Google Scholar
136b Bellina F. Cauteruccio S. Rossi R. Eur. J. Org. Chem. 2006, 1379

Google Scholar
136c Arai N. Takahashi M. Mitani M. Mori A. Synlett 2006, 3170

Google Scholar
136d Chiong HA. Daugulis O. Org. Lett. 2007, 9: 1449

Google Scholar
137 Hoarau C. de Kerdaniel ADF. Bracq N. Grandclaudon P. Couture A. Marsais F. Tetrahedron Lett. 2005, 46: 8573

Crossref Google Scholar
138 Čerňa I. Pohl R. Klepetářová B. Hocek M. Org. Lett. 2006, 8: 5389

Crossref Google Scholar
139 Parisien M. Valette D. Fagnou K. J. Org. Chem. 2005, 70: 7578

Crossref PubMed Google Scholar
140a Li W. Nelson DP. Jensen MS. Hoerrner RS. Javadi GJ. Cai D. Larsen RD. Org. Lett. 2003, 5: 4835

Google Scholar
140b Jensen MS. Hoerrner RS. Li W. Nelson DP. Javadi GJ. Dormer PG. Cai D. Larsen RD. J. Org. Chem. 2005, 70: 6034

Google Scholar
141a Ames DE. Bull D. Tetrahedron 1982, 38: 383

Google Scholar
141b Ames DE. Opalko A. Synthesis 1983, 234

Google Scholar
141c Ames DE. Opalko A. Tetrahedron 1984, 40: 1919

Google Scholar
141d Bringmann G. Jansen JR. Rink H.-P. Angew. Chem., Int. Ed. Engl. 1986, 25: 913

Google Scholar
141e Bringmann G. Holenz J. Weìrich R. Rübenacker M. Funke C. Boyd MR. Gulakowski RJ. François G. Tetrahedron 1998, 54: 497

Google Scholar
141f Bringmann G. Menche D. Acc. Chem. Res. 2001, 34: 615

Google Scholar
141g Deshpande PP. Martin OR. Tetrahedron Lett. 1990, 31: 6313

Google Scholar
141h Matsumoto T. Hosoya T. Suzuki K. J. Am. Chem. Soc. 1992, 114: 3568

Google Scholar
141i Hosoya T. Takashiro E. Matsumoto T. Suzuki K. J. Am. Chem. Soc. 1994, 116: 1004

Google Scholar
141j Leblanc M. Fagnou K. Org. Lett. 2005, 7: 2849

Google Scholar
141k Campeau L.-C. Parisien M. Jean A. Fagnou K. J. Am. Chem. Soc. 2006, 128: 581

Google Scholar
141l Campeau L.-C. Thansandote P. Fagnou K. Org. Lett. 2005, 7: 1857

Google Scholar
141m Bowie AL. Hughes CC. Trauner D. Org. Lett. 2005, 7: 5207

Google Scholar
141n García-Cuadrado D. Braga AAC. Maseras F. Echavarren AM. J. Am. Chem. Soc. 2006, 128: 1066

Google Scholar
141o García-Cuadrado D. de Mendoza P. Braga AAC. Maseras F. Echavarren AM. J. Am. Chem. Soc. 2007, 129: 6880

Google Scholar
142a van Helden RJ. Verberg G. Recl. Trav. Chim. Pays-Bas 1965, 84: 1263

Google Scholar
142b Davidson JM. Triggs C. Chem. Ind. 1966, 457

Google Scholar
143 Eberson L. Gomez-Gonzalez L. Acta Chim. Scand. 1973, 27: 1249

Crossref Google Scholar
144 Yoshimoto H. Itatani H. Bull. Chem. Soc. Jpn. 1973, 46: 2490

Crossref Google Scholar
145a Masui K. Ikegami H. Mori A. J. Am. Chem. Soc. 2004, 126: 5074

Google Scholar
145b Takahashi M. Masui K. Sekiguchi H. Kobayashi N. Mori A. Funahashi M. Tamaoki N. J. Am. Chem. Soc. 2006, 128: 10930

Google Scholar
146 Hull KL. Lanni EL. Sanford MS. J. Am. Chem. Soc. 2006, 128: 14047

Crossref PubMed Google Scholar
147a Li R. Jiang L. Lu W. Organometallics 2006, 25: 5973

Google Scholar
147b Stuart DR. Fagnou K. Science 2007, 316: 1172

Google Scholar
147c Dwight TA. Rue NR. Charyk D. Josselyn R. DeBoef B. Org. Lett. 2007, 9: 3137

Google Scholar
147d Hull KL. Sanford MS. J. Am. Chem. Soc. 2007, 129: 11904

Google Scholar
147e Stuart DR. Villemure E. Fagnou K. J. Am. Chem. Soc. 2007, 129: 12072

Google Scholar
148 Oi S. Fukita S. Inoue Y. Chem. Commun. 1998, 2439

Crossref Google Scholar
149a Kakiuchi F. Kan S. Igi K. Chatani N. Murai S. J. Am. Chem. Soc. 2003, 125: 1698

Google Scholar
149b Kakiuchi F. Matsuura Y. Kan S. Chatani N. J. Am. Chem. Soc. 2005, 127: 5936

Google Scholar
150 Ueura K. Satoh T. Miura M. Org. Lett. 2005, 7: 2229

Crossref Google Scholar
151a Catellani M. Marmiroli B. Fagnola MC. Acquotti D. J. Organomet. Chem. 1996, 507: 157

Google Scholar
151b Catellani M. Motti E. Paterlini L. Bocelli G. Righi L. J. Organomet. Chem. 1999, 580: 191

Google Scholar
151c Catellani M. Cugini F. Tetrahedron 1999, 55: 6595

Google Scholar
151d Catellani M. Motti E. Ghelli S. Chem. Commun. 2000, 2003

Google Scholar
151e Catellani M. Motti E. Baratta S. Org. Lett. 2001, 3: 3611

Google Scholar
151f Catellani M. Mealli C. Motti E. Paoli P. Perez-Carreño E. Pregosin PS. J. Am. Chem. Soc. 2002, 124: 4336

Google Scholar
151g Motti E. Ippomei G. Deledda S. Catellani M. Synthesis 2003, 2671

Google Scholar
151h Faccini F. Motti E. Catellani M. J. Am. Chem. Soc. 2004, 126: 78

Google Scholar
151i Ferraccioli R. Carenzi D. Rombolà O. Catellani M. Org. Lett. 2004, 6: 4759

Google Scholar
151j Motti E. Faccini F. Ferrari I. Catellani M. Ferraccioli R. Org. Lett. 2006, 8: 3967

Google Scholar
152a Lautens M. Piguel S. Angew. Chem. Int. Ed. 2000, 39: 1045

Google Scholar
152b Lautens M. Paquin J.-F. Piguel S. Dahlmann M. J. Org. Chem. 2001, 66: 8127

Google Scholar
152c Alberico D. Paquin J.-F. Lautens M. Tetrahedron 2005, 61: 6283

Google Scholar
152d Martins A. Marquardt U. Kasravi N. Alberico D. Lautens M. J. Org. Chem. 2006, 71: 4937

Google Scholar
152e Mitsudo K. Thansandote P. Wilhelm T. Mariampillai B. Lautens M. Org. Lett. 2006, 8: 3939

Google Scholar
153a Pache S. Lautens M. Org. Lett. 2003, 5: 4827

Google Scholar
153b Jafarpour F. Lautens M. Org. Lett. 2006, 8: 3601

Google Scholar
153c Alberico D. Lautens M. Synlett 2006, 2969

Google Scholar
153d Alberico D. Rudolph A. Lautens M. J. Org. Chem. 2007, 72: 775

Google Scholar
153e Rudolph A. Rackelmann N. Lautens M. Angew. Chem. Int. Ed. 2007, 46: 1485

Google Scholar
154a Bressy C. Alberico D. Lautens M. J. Am. Chem. Soc. 2005, 127: 13148

Google Scholar
154b Blaszykowski C. Aktoudianakis E. Bressy C. Alberico D. Lautens M. Org. Lett. 2006, 8: 2043

Google Scholar
154c Martins A. Alberico D. Lautens M. Org. Lett. 2006, 8: 4827

Google Scholar
155a Wilhelm T. Lautens M. Org. Lett. 2005, 7: 4053

Google Scholar
155b Mariampillai B. Alberico D. Bidau V. Lautens M. J. Am. Chem. Soc. 2006, 128: 14436

Google Scholar
156a Campo MA. Larock RC. J. Am. Chem. Soc. 2002, 124: 14326

Google Scholar
156b Campo MA. Huang Q. Yao T. Tian Q. Larock RC. J. Am. Chem. Soc. 2003, 125: 11506

Google Scholar
156c Huang Q. Campo MA. Yao T. Tian Q. Larock RC. J. Org. Chem. 2004, 69: 8251

Google Scholar
156d Zhao J. Larock RC. Org. Lett. 2005, 7: 701

Google Scholar
156e Zhao J. Larock RC. J. Org. Chem. 2006, 71: 5340

Google Scholar
157 Singh A. Sharp PR. J. Am. Chem. Soc. 2006, 128: 5998

Crossref PubMed Google Scholar
158a Oguma K. Miura M. Satoh T. Nomura M. J. Am. Chem. Soc. 2000, 122: 10464

Google Scholar
158b Hayashi T. Inoue K. Taniguchi N. Ogasawara M. J. Am. Chem. Soc. 2001, 123: 9918

Google Scholar
158c Oguma K. Miura M. Satoh T. Nomura M. J. Organomet. Chem. 2002, 648: 297

Google Scholar
158d Shintani R. Okamoto K. Hayashi T. J. Am. Chem. Soc. 2005, 127: 2872

Google Scholar
158e Yamabe H. Mizuno A. Kusama H. Iwasawa N. J. Am. Chem. Soc. 2005, 127: 3248

Google Scholar
159a Yi CS. Yun SY. Guzei IA. J. Am. Chem. Soc. 2005, 127: 5782

Google Scholar
159b Yi CS. Yun SY. J. Am. Chem. Soc. 2005, 127: 17000

Google Scholar
160 Keen AL. Doster M. Johnson SA. J. Am. Chem. Soc. 2007, 129: 810

Crossref PubMed Google Scholar
161a Kuninobu Y. Nishina Y. Nakagawa C. Takai K. J. Am. Chem. Soc. 2006, 128: 12376

Google Scholar
161b Kuninobu Y. Tokunaga Y. Takai K. Chem. Lett. 2007, 36: 872

Google Scholar
161c Kuninobu Y. Nishina Y. Takai K. Tetrahedron 2007, 63: 8463

Google Scholar
161d Kuninobu Y. Nishina Y. Takeuchi T. Takai K. Angew. Chem. Int. Ed. 2007, 46: 6518

Google Scholar