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
Synthesis 2008(19): 3013-3039
DOI: 10.1055/s-2008-1067256
DOI: 10.1055/s-2008-1067256
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New YorkTransition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage
Further Information
Received
29 February 2008
Publication Date:
05 September 2008 (online)
Publication History
Publication Date:
05 September 2008 (online)
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
- 1
Blanksby SJ.Ellison GB. Acc. Chem. Res. 2003, 36: 255 - 2
Kleiman JP.Dubeck M. J. Am. Chem. Soc. 1963, 85: 1544 - 3a
Chatt J.Watson HW. J. Chem. Soc. 1962, 2545 - 3b
Chatt J.Davidson JM. J. Chem. Soc. 1965, 843 - 4a
Bergman RG. Science 1984, 223: 902 - 4b
Crabtree RH. Chem. Rev. 1985, 85: 245 - 4c
Shilov AE.Shul’pin GB. Chem. Rev. 1997, 97: 2879 - 4d
Labinger JA.Bercaw JE. Nature 2002, 417: 507 - 4e
Bergman RG. Nature 2007, 446: 391 - 5
Fujiwara Y.Moritani I.Danno S.Asano R.Teranishi S. J. Am. Chem. Soc. 1969, 91: 7166 - 6
Hong P.Yamazaki H.Sonogashira K.Hagihara N. Chem. Lett. 1978, 7: 535 - 7
Lewis LN.Smith JF. J. Am. Chem. Soc. 1986, 108: 2728 - 8a
Murai S.Kakiuchi F.Sekine S.Tanaka Y.Kamatani A.Sonoda M.Chatani N. Nature 1993, 366: 529 - 8b
Murai S.Kakiuchi F.Sekine S.Tanaka Y.Kamatani A.Sonoda M.Chatani N. Pure Appl. Chem. 1994, 66: 1527 - 8c
Kakiuchi F.Sekine S.Tanaka Y.Kamatani A.Sonoda M.Chatani N.Murai S. Bull. Chem. Soc. Jpn. 1995, 68: 62 - 8d
Sonoda M.Kakiuchi F.Chatani N.Murai S. J. Organomet. Chem. 1995, 504: 151 - 8e
Sonoda M.Kakiuchi F.Chatani N.Murai S. Bull. Chem. Soc. Jpn. 1997, 70: 3117 - 8f
Kakiuchi F.Murai S. Org. Synth. 2003, 80: 104 - 9a
Kakiuchi F.Murai S. Top. Organomet. Chem. 1999, 3: 47 - 9b
Dyker G. Angew. Chem. Int. Ed. 1999, 38: 1698 - 9c
Ritleng V.Sirlin C.Pfeffer M. Chem. Rev. 2002, 102: 1731 - 9d
Kakiuchi F.Chatani N. Adv. Synth. Catal. 2003, 345: 1077 - 9e
Park YJ.Jun C.-H. Bull. Korean Chem. Soc. 2005, 26: 871 - 9f
Godula K.Sames D. Science 2006, 312: 67 - 10a
Jordan RF.Taylor DF. J. Am. Chem. Soc. 1989, 111: 778 - 10b
Rodewald S.Jordan RF. J. Am. Chem. Soc. 1994, 116: 4491 - 11a
Guo H.Tapsak MA.Weber WP. Macromolecules 1995, 28: 4714 - 11b
Lu P.Paulasaari J.Jin K.Bau R.Weber WP. Organometallics 1998, 17: 584 - 11c
Gupta SK.Weber WP. Macromolecules 2000, 33: 108 - 12
Grigg R.Savic V. Tetrahedron Lett. 1997, 38: 5737 - 13a
Harris PWR.Woodgate PD. J. Organomet. Chem. 1996, 506: 339 - 13b
Harris PWR.Woodgate PD. J. Organomet. Chem. 1997, 530: 211 - 13c
Harris PWR.Woodgate PD. Tetrahedron 2000, 56: 4001 - 14a
Grellier M.Vendier L.Chaudret B.Albinati A.Rizzato S.Mason S.Sabo-Etienne S. J. Am. Chem. Soc. 2005, 127: 17592 - 14b
Guari Y.Castellanos A.Sabo-Etienne S.Chaudret B. J. Mol. Catal. A: Chem. 2004, 212: 77 - 15a
Busch S.Leitner W. Chem. Commun. 1999, 2305 - 15b
Busch S.Leitner W. Adv. Synth. Catal. 2001, 343: 192 - 16
Martinez R.Chevalier R.Darses S.Genet J.-P. Angew. Chem. Int. Ed. 2006, 45: 8232 - 17a
Matsubara T.Koga N.Musaev DG.Morokuma K. J. Am. Chem. Soc. 1998, 120: 12692 - 17b
Matsubara T.Koga N.Musaev DG.Morokuma K. Organometallics 2000, 19: 2318 - 18
Lenges CP.Brookhart M. J. Am. Chem. Soc. 1999, 121: 6616 - 19
Jazzar RFR.Mahon MF.Whittlesey MK. Organometallics 2001, 20: 3745 - 20
Drouin SD.Amoroso D.Yap GPA.Fogg DE. Organometallics 2002, 21: 1042 - 21a
Sonoda M.Kakiuchi F.Kamatani A.Chatani N.Murai S. Chem. Lett. 1996, 109 - 21b
Kakiuchi F.Ohtaki H.Sonoda M.Chatani N.Murai S. Chem. Lett. 2001, 918 - 22
Aufdenblatten R.Diezi S.Togni A. Monatsh. Chem. 2000, 131: 1345 - 23
Tsuji J.Ohno K. Tetrahedron Lett. 1965, 3969 - 24a
Bosnich B. Acc. Chem. Res. 1998, 31: 667 - 24b
Jun C.-H.Jo E.-A.Park J.-W. Eur. J. Org. Chem. 2007, 1869 - 25
Kakiuchi F.Sato T.Igi K.Chatani N.Murai S. Chem. Lett. 2001, 386 - 26a
Kakiuchi F.Yamauchi M.Chatani N.Murai S. Chem. Lett. 1996, 111 - 26b
Kakiuchi F.Sato T.Tsujimoto T.Yamauchi M.Chatani N.Murai S. Chem. Lett. 1998, 1053 - 27a
Lim Y.-G.Han J.-S.Yang S.-S.Chun JH. Tetrahedron Lett. 2001, 42: 4853 - 27b
Lim Y.-G.Koo BT. Tetrahedron Lett. 2005, 46: 7997 - 28a
Jun C.-H.Hong J.-B.Kim Y.-H.Chung K.-Y. Angew. Chem. Int. Ed. 2000, 39: 3440 - 28b
Lim S.-G.Ahn J.-A.Jun C.-H. Org. Lett. 2004, 6: 4687 - 28c
Yoon JH.Park YJ.Lee JH.Yoo J.Jun C.-H. Org. Lett. 2005, 7: 2889 - 28d
Jo E.-A.Cho E.-G.Jun C.-H. Synlett 2007, 1059 - 29
Kakiuchi F.Tsujimoto T.Sonoda M.Chatani N.Murai S. Synlett 2001, 948 - 30a
Lim Y.-G.Kim YH.Kang J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267 - 30b
Lim Y.-G.Kang J.-B.Kim YH. J. Chem. Soc., Perkin Trans. 1 1996, 2201 - 31
Kakiuchi F.Le Gendre P.Yamada A.Ohtaki H.Murai S. Tetrahedron: Asymmetry 2000, 11: 2647 - 32
Kakiuchi F.Sato T.Yamauchi M.Chatani N.Murai S. Chem. Lett. 1999, 19 - 33
Kakiuchi F.Sonoda M.Tsujimoto T.Chatani N.Murai S. Chem. Lett. 1999, 1083 - 34a
Tan KL.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2002, 124: 3202 - 34b
Tan KL.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2002, 124: 13964 - 34c
Tan KL.Park S.Ellman JA.Bergman RG. J. Org. Chem. 2004, 69: 7329 - 34d
Wiedemann SH.Bergman RG.Ellman JA. Org. Lett. 2004, 6: 1685 - 34e
Wiedemann SH.Ellman JA.Bergman RG. J. Org. Chem. 2006, 71: 1969 - 34f
Wiedemann SH.Lewis JC.Ellman JA.Bergman RG. J. Am. Chem. Soc. 2006, 128: 2452 - 34g
Lewis JC.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2007, 129: 5332 - 35a
Matsumoto T.Taube DJ.Periana RA.Taube H.Yoshida H. J. Am. Chem. Soc. 2000, 122: 7414 - 35b
Oxgaard J.Muller RP.Goddard WA. J. Am. Chem. Soc. 2004, 126: 352 - 35c
Oxgaard J.Periana RA.Goddard WA. J. Am. Chem. Soc. 2004, 126: 11658 - 35d
Bhalla G.Liu XY.Oxgaard J.Goddard WA. J. Am. Chem. Soc. 2005, 127: 11372 - 35e
Bhalla G.Oxgaard J.Goddard WA. Organometallics 2005, 24: 3229 - 36a
Lail M.Bell CM.Conner D.Cundari TR.Gunnoe TB.Petersen JL. Organometallics 2004, 23: 5007 - 36b
Foley NA.Lail M.Lee JP.Gunnoe TB.Cundari TR.Petersen JL. J. Am. Chem. Soc. 2007, 129: 6765 - 36c
DeYonker NJ.Foley NA.Cundari TR.Gunnoe TB.Petersen JL. Organometallics 2007, 26: 6604 - 36d
Gunnoe TB. Eur. J. Inorg. Chem. 2007, 1185 - 37
Trost BM.Imi K.Davies IW. J. Am. Chem. Soc. 1995, 117: 5371 - 38a
Kakiuchi F.Tanaka Y.Sato T.Chatani N.Murai S. Chem. Lett. 1995, 679 - 38b
Sato T.Kakiuchi F.Chatani N.Murai S. Chem. Lett. 1998, 893 - 39a
Lim Y.-G.Kang J.-B.Kim YH. Chem. Commun. 1996, 585 - 39b
Lim Y.-G.Kang J.-B.Kim YH. J. Chem. Soc., Perkin Trans. 1 1998, 699 - 39c
Lim Y.-G.Kang J.-B.Koo BT. Tetrahedron Lett. 1999, 40: 7691 - 39d
Lim Y.-G.Kang J.-B.Lee K.Kim YH. Heteroat. Chem. 2002, 13: 346 - 40
Diamond SE.Szalkiewicz A.Mares F. J. Am. Chem. Soc. 1979, 101: 490 - 41
Beller M.Thiel OR.Trauthwein H.Hartung CG. Chem. Eur. J. 2000, 6: 2513 - 42a
Cho CS.Lim HK.Shim SC.Kim TJ.Chi H.-J. Chem. Commun. 1998, 995 - 42b
Cho CS.Kim JS.Oh BH.Kim T.-J.Shim SC.Yoon NS. Tetrahedron 2000, 56: 7747 - 43a
Jacob J.Cavalier CM.Jones WD.Godleski SA.Valent RR. J. Mol. Catal. A: Chem. 2002, 182-183: 565 - 43b
Li L.Jones WD. J. Am. Chem. Soc. 2007, 129: 10707 - 44
Nugent WA.Ovenall DW.Holmes SJ. Organometallics 1983, 2: 161 - 45
Jun C.-H.Hwang D.-C.Na S.-J. Chem. Commun. 1998, 1405 - 46
Chatani N.Asaumi T.Yorimitsu S.Ikeda T.Kakiuchi F.Murai S. J. Am. Chem. Soc. 2001, 123: 10935 - 47a
Fujii N.Kakiuchi F.Chatani N.Murai S. Chem. Lett. 1996, 939 - 47b
Fujii N.Kakiuchi F.Yamada A.Chatani N.Murai S. Chem. Lett. 1997, 425 - 47c
Fujii N.Kakiuchi F.Yamada A.Chatani N.Murai S. Bull. Chem. Soc. Jpn. 1998, 71: 285 - 48a
Tan KL.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2001, 123: 2685 - 48b
Thalji RK.Ahrendt KA.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2001, 123: 9692 - 48c
Thalji RK.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2004, 126: 7192 - 48d
Rech JC.Yato M.Duckett D.Ember B.LoGrasso PV.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2007, 129: 490 - 49
DeBoef B.Pastine SJ.Sames D. J. Am. Chem. Soc. 2004, 126: 6556 - 50a
Hong P.Cho B.-R.Yamazaki H. Chem. Lett. 1979, 9: 339 - 50b
Hong P.Cho B.-R.Yamazaki H. Chem. Lett. 1980, 10: 507 - 50c
Yamazaki H.Hong P. J. Mol. Catal. 1983, 21: 133 - 51a
Halbritter G.Knoch F.Wolski A.Kisch H. Angew. Chem., Int. Ed. Engl. 1994, 33: 1603 - 51b
Dürr U.Kisch H. Synlett 1997, 1335 - 52a
Kakiuchi F.Yamamoto Y.Chatani N.Murai S. Chem. Lett. 1995, 681 - 52b
Kakiuchi F.Uetsuhara T.Tanaka Y.Chatani N.Murai S. J. Mol. Catal. A: Chem. 2002, 511: 182 - 53
Harris PWR.Rickard CEF.Woodgate PD. J. Organomet. Chem. 1999, 589: 168 - 54
Londergan TM.You Y.Thompson ME.Weber WP. Macromolecules 1998, 31: 2784 - 55
Satoh T.Nishinaka Y.Miura M.Nomura M. Chem. Lett. 1999, 615 - 56
Lim S.-G.Lee JH.Moon CW.Hong J.-B.Jun C.-H. Org. Lett. 2003, 5: 2759 - 57
Lim Y.-G.Lee K.-H.Koo BT.Kang J.-B. Tetrahedron Lett. 2001, 42: 7609 - 58a
Kuninobu Y.Kawata A.Takai K. J. Am. Chem. Soc. 2005, 127: 13498 - 58b
Kuninobu Y.Tokunaga Y.Kawata A.Takai K. J. Am. Chem. Soc. 2006, 128: 202 - 59a
Ueura K.Satoh T.Miura M. Org. Lett. 2007, 9: 1407 - 59b
Ueura K.Satoh T.Miura M. J. Org. Chem. 2007, 72: 5362 - 60a
Tsukada N.Mitsuboshi T.Setoguchi H.Inoue Y. J. Am. Chem. Soc. 2003, 125: 12102 - 60b
Tsukada N.Murata K.Inoue Y. Tetrahedron Lett. 2005, 46: 7515 - 61
Nakao Y.Yada A.Ebata S.Hiyama T. J. Am. Chem. Soc. 2007, 129: 2428 - 62a
Sakaguchi S.Kubo T.Ishii Y. Angew. Chem. Int. Ed. 2001, 40: 2534 - 62b
Ishii Y.Sakaguchi S. Bull. Chem. Soc. Jpn. 2004, 77: 909 - 63a
Tunge JA.Foresee LN. Organometallics 2005, 24: 6440 - 63b
Fürstner A.Davies PW. Angew. Chem. Int. Ed. 2007, 46: 3410 - 64a
Hong P.Yamazaki H. Chem. Lett. 1979, 1335 - 64b
Lin Y.Ma D.Lu X. Tetrahedron Lett. 1987, 28: 3249 - 65
Tsuji J.Nagashima H. Tetrahedron 1984, 40: 2699 - 66a
Yokota T.Tani M.Sakaguchi S.Ishii Y. J. Am. Chem. Soc. 2003, 125: 1476 - 66b
Tani M.Sakaguchi S.Ishii Y. J. Org. Chem. 2004, 69: 1221 - 66c
Yamada T.Sakaguchi S.Ishii Y. J. Org. Chem. 2005, 70: 5471 - 67
Dams M.De Vos DE.Celen S.Jacobs PA. Angew. Chem. Int. Ed. 2003, 42: 3512 - 68a
Matsumoto T.Yoshida H. Chem. Lett. 2000, 1064 - 68b
Matsumoto T.Periana RA.Taube DJ.Yoshida H. J. Catal. 2002, 206: 272 - 68c
Weissman H.Song X.Milstein D. J. Am. Chem. Soc. 2001, 123: 337 - 69
Mikami K.Hatano M.Terada M. Chem. Lett. 1999, 55 - 70
Miura M.Tsuda T.Satoh T.Nomura M. Chem. Lett. 1997, 1103 - 71
Miura M.Tsuda T.Satoh T.Pivsa-Art S.Nomura M. J. Org. Chem. 1998, 63: 5211 - 72a
Boele MDK.van Strijdonck GPF.de Vries AHM.Kamer PCJ.de Vries JD.van Leeuwen PWNM. J. Am. Chem. Soc. 2002, 124: 1586 - 72b
Boele MDK.van Strijdonck GPF.de Vries AHM.Kamer PCJ.de Vries JG.van Leeuwen PWNM. J. Am. Chem. Soc. 2005, 127: 4156 - 73
Cai G.Fu Y.Li Y.Wan X.Shi Z. J. Am. Chem. Soc. 2007, 129: 7666 - 74a
Grimster NP.Gauntlett C.Godfrey CRA.Gaunt MJ. Angew. Chem. Int. Ed. 2005, 44: 3125 - 74b
Beck EM.Grimster NP.Hatley R.Gaunt MJ. J. Am. Chem. Soc. 2006, 128: 2528 - 75a
Oi S.Fukita S.Hirata N.Watanuki N.Miyano S.Inoue Y. Org. Lett. 2001, 3: 2579 - 75b
Oi S.Ogino Y.Fukita S.Inoue Y. Org. Lett. 2002, 4: 1783 - 75c
Oi S.Aizawa E.Ogino Y.Inoue Y. J. Org. Chem. 2005, 70: 3113 - 76
Zaitsev VG.Daugulis O. J. Am. Chem. Soc. 2005, 127: 4156 - 77
Matsuura Y.Tamura M.Kochi T.Sato M.Chatani N.Kakiuchi F. J. Am. Chem. Soc. 2007, 129: 9858 - 78
Ueno S.Chatani N.Kakiuchi F. J. Org. Chem. 2007, 72: 3600 - 79a
Fisher BJ.Eisenberg R. Organometallics 1983, 2: 764 - 79b
Kunin AJ.Eisenberg R. J. Am. Chem. Soc. 1986, 108: 535 - 79c
Gordon EM.Eisenberg R. J. Mol. Catal. 1988, 45: 57 - 79d
Kunin AJ.Eisenberg R. Organometallics 1988, 7: 2124 - 80a
Sakakura T.Tanaka M. Chem. Lett. 1987, 249 - 80b
Sakakura T.Tanaka M. J. Chem. Soc., Chem. Commun. 1987, 758 - 80c
Sakakura T.Tanaka M. Chem. Lett. 1987, 1113 - 80d
Sakakura T.Sodeyama T.Sasaki K.Wada K.Tanaka M. J. Am. Chem. Soc. 1990, 112: 7221 - 80e
Tanaka M.Sakakura T. Pure Appl. Chem. 1990, 62: 1147 - 81
Boyd SE.Field LD.Partridge MG. J. Am. Chem. Soc. 1994, 116: 9492 - 82
Rosini GP.Boese WT.Goldman AS. J. Am. Chem. Soc. 1994, 116: 9498 - 83
Bridgewater JS.Lee B.Bernhard S.Schoonover JR.Ford PC. Organometallics 1997, 16: 5592 - 84
Koga N.Morokuma K. J. Phys. Chem. 1990, 94: 5454 - 85a
Margl P.Ziegler T.Blöchl PE. J. Am. Chem. Soc. 1995, 117: 12625 - 85b
Margl P.Ziegler T.Blöchl PE. J. Am. Chem. Soc. 1996, 118: 5412 - 86a
Jones WD.Kosar WP. J. Am. Chem. Soc. 1986, 108: 5640 - 86b
Hsu GC.Kosar WP.Jones WD. Organometallics 1994, 13: 385 - 87a
Jones WD.Foster GP.Putinas JM. J. Am. Chem. Soc. 1987, 109: 5047 - 87b
Jones WD.Hessell ET. Organometallics 1990, 9: 718 - 88
Tanaka M.Sakakura T.Tokunaga Y.Sodeyama T. Chem. Lett. 1987, 2373 - 89
Moore EJ.Pretzer WR.O’Connell TJ.Harris J.LaBounty L.Chou L.Grimmer SC. J. Am. Chem. Soc. 1992, 114: 5888 - 90a
Chatani N.Fukuyama T.Kakiuchi F.Murai S. J. Am. Chem. Soc. 1996, 118: 493 - 90b
Chatani N.Fukuyama T.Tatamidani H.Kakiuchi F.Murai S. J. Org. Chem. 2000, 65: 4039 - 91
Fukuyama T.Chatani N.Tatsumi J.Kakiuchi F.Murai S. J. Am. Chem. Soc. 1998, 120: 11522 - 92a
Chatani N.Ie Y.Kakiuchi F.Murai S. J. Org. Chem. 1997, 62: 2604 - 92b
Chatani N.Uemura T.Asaumi T.Ie Y.Kakiuchi F.Murai S. Can. J. Chem. 2005, 83: 755 - 92c
Imoto S.Uemura T.Kakiuchi F.Chatani N. Synlett 2007, 170 - 93
Ie Y.Chatani N.Ogo T.Marshall DR.Fukuyama T.Kakiuchi F.Murai S. J. Org. Chem. 2000, 65: 1475 - 94
Fukuyama T.Chatani N.Kakiuchi F.Murai S. J. Org. Chem. 1997, 62: 5647 - 95
Chatani N.Yorimitsu S.Asaumi T.Kakiuchi F.Murai S. J. Org. Chem. 2002, 67: 7557 - 96
Szewczyk JW.Zuckerman RL.Bergman RG.Ellman JA. Angew. Chem. Int. Ed. 2001, 40: 216 - 97
Chatani N.Asaumi T.Ikeda T.Yorimitsu S.Ishii Y.Kakiuchi F.Murai S. J. Am. Chem. Soc. 2000, 122: 12882 - 98
Ishii Y.Chatani N.Kakiuchi F.Murai S. Organometallics 1997, 16: 3615 - 99
Ishii Y.Chatani N.Kakiuchi F.Murai S. Tetrahedron Lett. 1997, 38: 7565 - 100a
Satoh T.Miura M.Nomura M. J. Organomet. Chem. 2002, 653: 161 - 100b
Catellani M. Synlett 2003, 298 - 100c
Campeau L.-C.Fagnou K. Chem. Commun. 2006, 1253 - 100d
Daugulis O.Zaitsev VG.Shabashov D.Pham Q.-N.Lazareva A. Synlett 2006, 3382 - 100e
Satoh T.Miura M. Chem. Lett. 2007, 36: 200 - 100f
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 174 - 100g
Ackermann L. Synlett 2007, 507 - 100h
Pascual S.de Mendoza P.Echavarren AM. Org. Biomol. Chem. 2007, 5: 2727 - 101
Nakamura N.Tajima Y.Sakai K. Heterocycles 1982, 17: 235 - 102a
Catellani M.Chiusoli GP. J. Organomet. Chem. 1985, 286: 13 - 102b
Catellani M.Chiusoli GP.Castagnoli C. J. Organomet. Chem. 1991, 407: C30 - 103a
Reiser O.Weber M.de Meijere A. Angew. Chem., Int. Ed. Engl. 1989, 28: 1037 - 103b
Albrecht K.Reiser O.Weber M.Knieriem B.de Meijere A. Tetrahedron 1994, 50: 383 - 104a
Satoh T.Kawamura Y.Miura M.Nomura M. Angew. Chem., Int. Ed. Engl. 1997, 36: 1740 - 104b
Satoh T.Inoh J.-i.Kawamura Y.Kawamura Y.Miura M.Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 2239 - 105
Kawamura Y.Satoh T.Miura M.Nomura M. Chem. Lett. 1998, 961 - 106a
Bedford RB.Coles SJ.Hursthouse MB.Limmert ME. Angew. Chem. Int. Ed. 2003, 42: 112 - 106b
Bedford RB.Limmert ME. J. Org. Chem. 2003, 68: 8669 - 107
Oi S.Watanabe S.-i.Fukita S.Inoue Y. Tetrahedron Lett. 2003, 44: 8665 - 108
Lewis JC.Wu J.Bergman RG.Ellman JA. Organometallics 2005, 24: 5737 - 109
Satoh T.Kametani Y.Terao Y.Miura M.Nomura M. Tetrahedron Lett. 1999, 40: 5345 - 110
Kametani Y.Satoh T.Miura M.Nomura M. Tetrahedron Lett. 2000, 41: 2655 - 111
Terao Y.Kametani Y.Wakui H.Satoh T.Miura M.Nomura M. Tetrahedron 2001, 57: 5967 - 112a
Shabashov D.Daugulis O. Org. Lett. 2006, 8: 4947 - 112b
Shabashov D.Daugulis O. J. Org. Chem. 2007, 72: 7720 ; and references cited therein - 113
Okazawa T.Satoh T.Miura M.Nomura M. J. Am. Chem. Soc. 2002, 124: 5286 - 114
Glover B.Harvey KA.Liu B.Sharp MJ.Tymoschenko MF. Org. Lett. 2003, 5: 301 - 115
Ackermann L. Org. Lett. 2005, 7: 3123 - 116
Ackermann L.Althammer A.Born R. Angew. Chem. Int. Ed. 2006, 45: 2619 - 117a
Lafrance M.Rowley CN.Woo TK.Fagnou K. J. Am. Chem. Soc. 2006, 128: 8754 - 117b
Lafrance M.Fagnou K. J. Am. Chem. Soc. 2006, 128: 16496 - 117c
Fujita K.-i.Nonogawa M.Yamaguchi R. Chem. Commun. 2006, 1926 - 118a
Campeau L.-C.Rousseaux S.Fagnou K. J. Am. Chem. Soc. 2005, 127: 18020 - 118b
Leclerc J.-P.Fagnou K. Angew. Chem. Int. Ed. 2006, 45: 7781 - 119
Miura M.Pivsa-Art S.Dyker G.Heiermann J.Satoh T.Nomura M. Chem. Commun. 1998, 1889 - 120a
Kalyani D.Deprez NR.Desai LV.Sanford MS. J. Am. Chem. Soc. 2005, 127: 7330 - 120b
Daugulis O.Zaitsev VG. Angew. Chem. Int. Ed. 2005, 44: 4046 - 120c
Deprez NR.Kalyani D.Krause A.Sanford MS. J. Am. Chem. Soc. 2006, 128: 4972 - 121
Oi S.Sakai K.Inoue Y. Org. Lett. 2005, 7: 4009 - 122a
Dyker G. Angew. Chem., Int. Ed. Engl. 1992, 31: 1023 - 122b
Dyker G. Angew. Chem., Int. Ed. Engl. 1994, 33: 103 - 123
Inoh J.-I.Satoh T.Pivsa-Art S.Miura M.Nomura M. Tetrahedron Lett. 1998, 39: 4673 - 124a
Shabashov D.Daugulis O. Org. Lett. 2005, 7: 3657 - 124b
Zaitsev VG.Shabashov D.Daugulis O. J. Am. Chem. Soc. 2005, 127: 13154 - 125a
Akita Y.Itagaki Y.Takizawa S.Ohta A. Chem. Pharm. Bull. 1989, 37: 1477 - 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 - 126
Pivsa-Art S.Satoh T.Kawamura Y.Miura M.Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467 - 127
Lavenot L.Gozzi C.Ilg K.Orlova I.Penalva V.Lemaire M. J. Organomet. Chem. 1998, 567: 49 - 128
Masui K.Mori A.Okano K.Takamura K.Kinoshita M.Ikeda T. Org. Lett. 2004, 6: 2011 - 129
Yokooji A.Satoh T.Miura M.Nomura M. Tetrahedron 2004, 60: 6757 - 130
Kobayashi K.Sugie A.Takahashi M.Masui K.Mori A. Org. Lett. 2005, 7: 5083 - 131
McClure MS.Glover B.McSorley E.Millar A.Osterhout MH.Roschangar F. Org. Lett. 2001, 3: 1677 - 132
Nakano M.Satoh T.Miura M. J. Org. Chem. 2006, 71: 8309 - 133
Yanagisawa S.Sudo T.Noyori R.Itami K. J. Am. Chem. Soc. 2006, 128: 11748 - 134
Park C.-H.Ryabova V.Seregin IV.Sromek AW.Gevorgyan V. Org. Lett. 2004, 6: 1159 - 135a
Mori A.Sekiguchi A.Masui K.Shimada T.Horie M.Osakada K.Kawamoto M.Ikeda T. J. Am. Chem. Soc. 2003, 125: 1700 - 135b
Yokooji A.Okazawa T.Satoh T.Miura M.Nomura M. Tetrahedron 2003, 59: 5685 - 136a
Bellina F.Cauteruccio S.Mannina L.Rossi R.Viel S. J. Org. Chem. 2005, 70: 3997 - 136b
Bellina F.Cauteruccio S.Rossi R. Eur. J. Org. Chem. 2006, 1379 - 136c
Arai N.Takahashi M.Mitani M.Mori A. Synlett 2006, 3170 - 136d
Chiong HA.Daugulis O. Org. Lett. 2007, 9: 1449 - 137
Hoarau C.de Kerdaniel ADF.Bracq N.Grandclaudon P.Couture A.Marsais F. Tetrahedron Lett. 2005, 46: 8573 - 138
Čerňa I.Pohl R.Klepetářová B.Hocek M. Org. Lett. 2006, 8: 5389 - 139
Parisien M.Valette D.Fagnou K. J. Org. Chem. 2005, 70: 7578 - 140a
Li W.Nelson DP.Jensen MS.Hoerrner RS.Javadi GJ.Cai D.Larsen RD. Org. Lett. 2003, 5: 4835 - 140b
Jensen MS.Hoerrner RS.Li W.Nelson DP.Javadi GJ.Dormer PG.Cai D.Larsen RD. J. Org. Chem. 2005, 70: 6034 - 141a
Ames DE.Bull D. Tetrahedron 1982, 38: 383 - 141b
Ames DE.Opalko A. Synthesis 1983, 234 - 141c
Ames DE.Opalko A. Tetrahedron 1984, 40: 1919 - 141d
Bringmann G.Jansen JR.Rink H.-P. Angew. Chem., Int. Ed. Engl. 1986, 25: 913 - 141e
Bringmann G.Holenz J.Weìrich R.Rübenacker M.Funke C.Boyd MR.Gulakowski RJ.François G. Tetrahedron 1998, 54: 497 - 141f
Bringmann G.Menche D. Acc. Chem. Res. 2001, 34: 615 - 141g
Deshpande PP.Martin OR. Tetrahedron Lett. 1990, 31: 6313 - 141h
Matsumoto T.Hosoya T.Suzuki K. J. Am. Chem. Soc. 1992, 114: 3568 - 141i
Hosoya T.Takashiro E.Matsumoto T.Suzuki K. J. Am. Chem. Soc. 1994, 116: 1004 - 141j
Leblanc M.Fagnou K. Org. Lett. 2005, 7: 2849 - 141k
Campeau L.-C.Parisien M.Jean A.Fagnou K. J. Am. Chem. Soc. 2006, 128: 581 - 141l
Campeau L.-C.Thansandote P.Fagnou K. Org. Lett. 2005, 7: 1857 - 141m
Bowie AL.Hughes CC.Trauner D. Org. Lett. 2005, 7: 5207 - 141n
García-Cuadrado D.Braga AAC.Maseras F.Echavarren AM. J. Am. Chem. Soc. 2006, 128: 1066 - 141o
García-Cuadrado D.de Mendoza P.Braga AAC.Maseras F.Echavarren AM. J. Am. Chem. Soc. 2007, 129: 6880 - 142a
van Helden RJ.Verberg G. Recl. Trav. Chim. Pays-Bas 1965, 84: 1263 - 142b
Davidson JM.Triggs C. Chem. Ind. 1966, 457 - 143
Eberson L.Gomez-Gonzalez L. Acta Chim. Scand. 1973, 27: 1249 - 144
Yoshimoto H.Itatani H. Bull. Chem. Soc. Jpn. 1973, 46: 2490 - 145a
Masui K.Ikegami H.Mori A. J. Am. Chem. Soc. 2004, 126: 5074 - 145b
Takahashi M.Masui K.Sekiguchi H.Kobayashi N.Mori A.Funahashi M.Tamaoki N. J. Am. Chem. Soc. 2006, 128: 10930 - 146
Hull KL.Lanni EL.Sanford MS. J. Am. Chem. Soc. 2006, 128: 14047 - 147a
Li R.Jiang L.Lu W. Organometallics 2006, 25: 5973 - 147b
Stuart DR.Fagnou K. Science 2007, 316: 1172 - 147c
Dwight TA.Rue NR.Charyk D.Josselyn R.DeBoef B. Org. Lett. 2007, 9: 3137 - 147d
Hull KL.Sanford MS. J. Am. Chem. Soc. 2007, 129: 11904 - 147e
Stuart DR.Villemure E.Fagnou K. J. Am. Chem. Soc. 2007, 129: 12072 - 148
Oi S.Fukita S.Inoue Y. Chem. Commun. 1998, 2439 - 149a
Kakiuchi F.Kan S.Igi K.Chatani N.Murai S. J. Am. Chem. Soc. 2003, 125: 1698 - 149b
Kakiuchi F.Matsuura Y.Kan S.Chatani N. J. Am. Chem. Soc. 2005, 127: 5936 - 150
Ueura K.Satoh T.Miura M. Org. Lett. 2005, 7: 2229 - 151a
Catellani M.Marmiroli B.Fagnola MC.Acquotti D. J. Organomet. Chem. 1996, 507: 157 - 151b
Catellani M.Motti E.Paterlini L.Bocelli G.Righi L. J. Organomet. Chem. 1999, 580: 191 - 151c
Catellani M.Cugini F. Tetrahedron 1999, 55: 6595 - 151d
Catellani M.Motti E.Ghelli S. Chem. Commun. 2000, 2003 - 151e
Catellani M.Motti E.Baratta S. Org. Lett. 2001, 3: 3611 - 151f
Catellani M.Mealli C.Motti E.Paoli P.Perez-Carreño E.Pregosin PS. J. Am. Chem. Soc. 2002, 124: 4336 - 151g
Motti E.Ippomei G.Deledda S.Catellani M. Synthesis 2003, 2671 - 151h
Faccini F.Motti E.Catellani M. J. Am. Chem. Soc. 2004, 126: 78 - 151i
Ferraccioli R.Carenzi D.Rombolà O.Catellani M. Org. Lett. 2004, 6: 4759 - 151j
Motti E.Faccini F.Ferrari I.Catellani M.Ferraccioli R. Org. Lett. 2006, 8: 3967 - 152a
Lautens M.Piguel S. Angew. Chem. Int. Ed. 2000, 39: 1045 - 152b
Lautens M.Paquin J.-F.Piguel S.Dahlmann M. J. Org. Chem. 2001, 66: 8127 - 152c
Alberico D.Paquin J.-F.Lautens M. Tetrahedron 2005, 61: 6283 - 152d
Martins A.Marquardt U.Kasravi N.Alberico D.Lautens M. J. Org. Chem. 2006, 71: 4937 - 152e
Mitsudo K.Thansandote P.Wilhelm T.Mariampillai B.Lautens M. Org. Lett. 2006, 8: 3939 - 153a
Pache S.Lautens M. Org. Lett. 2003, 5: 4827 - 153b
Jafarpour F.Lautens M. Org. Lett. 2006, 8: 3601 - 153c
Alberico D.Lautens M. Synlett 2006, 2969 - 153d
Alberico D.Rudolph A.Lautens M. J. Org. Chem. 2007, 72: 775 - 153e
Rudolph A.Rackelmann N.Lautens M. Angew. Chem. Int. Ed. 2007, 46: 1485 - 154a
Bressy C.Alberico D.Lautens M. J. Am. Chem. Soc. 2005, 127: 13148 - 154b
Blaszykowski C.Aktoudianakis E.Bressy C.Alberico D.Lautens M. Org. Lett. 2006, 8: 2043 - 154c
Martins A.Alberico D.Lautens M. Org. Lett. 2006, 8: 4827 - 155a
Wilhelm T.Lautens M. Org. Lett. 2005, 7: 4053 - 155b
Mariampillai B.Alberico D.Bidau V.Lautens M. J. Am. Chem. Soc. 2006, 128: 14436 - 156a
Campo MA.Larock RC. J. Am. Chem. Soc. 2002, 124: 14326 - 156b
Campo MA.Huang Q.Yao T.Tian Q.Larock RC. J. Am. Chem. Soc. 2003, 125: 11506 - 156c
Huang Q.Campo MA.Yao T.Tian Q.Larock RC. J. Org. Chem. 2004, 69: 8251 - 156d
Zhao J.Larock RC. Org. Lett. 2005, 7: 701 - 156e
Zhao J.Larock RC. J. Org. Chem. 2006, 71: 5340 - 157
Singh A.Sharp PR. J. Am. Chem. Soc. 2006, 128: 5998 - 158a
Oguma K.Miura M.Satoh T.Nomura M. J. Am. Chem. Soc. 2000, 122: 10464 - 158b
Hayashi T.Inoue K.Taniguchi N.Ogasawara M. J. Am. Chem. Soc. 2001, 123: 9918 - 158c
Oguma K.Miura M.Satoh T.Nomura M. J. Organomet. Chem. 2002, 648: 297 - 158d
Shintani R.Okamoto K.Hayashi T. J. Am. Chem. Soc. 2005, 127: 2872 - 158e
Yamabe H.Mizuno A.Kusama H.Iwasawa N. J. Am. Chem. Soc. 2005, 127: 3248 - 159a
Yi CS.Yun SY.Guzei IA. J. Am. Chem. Soc. 2005, 127: 5782 - 159b
Yi CS.Yun SY. J. Am. Chem. Soc. 2005, 127: 17000 - 160
Keen AL.Doster M.Johnson SA. J. Am. Chem. Soc. 2007, 129: 810 - 161a
Kuninobu Y.Nishina Y.Nakagawa C.Takai K. J. Am. Chem. Soc. 2006, 128: 12376 - 161b
Kuninobu Y.Tokunaga Y.Takai K. Chem. Lett. 2007, 36: 872 - 161c
Kuninobu Y.Nishina Y.Takai K. Tetrahedron 2007, 63: 8463 - 161d
Kuninobu Y.Nishina Y.Takeuchi T.Takai K. Angew. Chem. Int. Ed. 2007, 46: 6518