Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

D. W. Slocum; Phillip Shelton; Kelley M. Moran

doi:10.1055/s-2005-918495

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 2005(20): 3477-3498
DOI: 10.1055/s-2005-918495

REVIEW

Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

D. W. Slocum*, Phillip Shelton, Kelley M. Moran
Department of Chemistry, Western Kentucky University, 1906 College Heights Blvd, Bowling Green, KY 42101-1079, USA
Fax: +1(270)7455361; e-Mail: Donald.Slocum@wku.edu;

Further Information

Publication History

Received 27 June 2005
Publication Date:
24 November 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Introduction of a halogen (F, Cl, Br, I) or a chalcogen (O, S, Se, Te) via the intermediacy of an aryllithium or hetaryllithium is reviewed. Representative examples are presented to demonstrate the range of substituted aromatic compounds accessible via formation of the lithio-intermediate followed by treatment with an appropriate derivatizing agent. Where possible, the merits and the limitations of the various reagents utilized for introduction of a specific halogen or chalcogen are discussed.

1 Background
2 Halogenation
2.1 Fluorination
2.2 Chlorination
2.3 Bromination
2.4 Iodination
2.5 Conclusions Regarding Halogenations
3 Chalcogenation
3.1 Hydroxylation
3.2 Introduction of Sulfur
3.3 Introduction of Selenium
3.4 Introduction of Tellurium
3.5 Conclusions Regarding Chalcogenations
4 General Conclusions

Key words

aromatic - chalcogens - halogens - lithiations - metalations

References

Relevant reviews of hydrogen-lithium exchange (DoM):
1a Slocum DW. Sugarman DI. Adv. Chem. Ser. 1974, 130: 232

Google Scholar
1b Wakefield BJ. The Chemistry of Organolithium Compounds Pergamon Press; New York: 1974. p.26-50

Google Scholar
1c Gschwend HW. Rodriguez HR. Org. React. 1979, 26: 1

Google Scholar
1d Wakefield BJ. Organolithium Methods Academic Press; New York: 1988.

Google Scholar
1e Narasimhan NS. Mali RS. Top. Curr. Chem. 1987, 138: 63

Google Scholar
1f Snieckus V. Chem. Rev. 1990, 90: 879

Google Scholar
1g Quéguiner G. Marsais F. Snieckus V. Epsztain J. Adv. Heterocycl. Chem. 1991, 523: 187

Google Scholar
1h Clayden J. Organolithiums: Selectivity for Synthesis Pergamon Press; Oxford: 2002.

Google Scholar
1i Clayden J. In The Chemistry of Organolithium Compounds Rappoport Z. Marek I. John Wiley & Sons, Ltd.; West Sussex: 2004. Chap. 10.

Google Scholar
Relevant reviews of halogen-lithium exchange:
2a Wakefield BG. Organolithium Methods - Best Synthetic Methods Academic Press; New York: 1988.

Crossref Google Scholar
2b Wakefield BG. The Chemistry of Organolithium Compounds Pergamon Press; New York: 1974. p.51-65

Crossref Google Scholar
2c Jones RG. Gilman H. Org. React. 1951, 6: 339

Crossref Google Scholar
2d Parham WE. Bradsher CK. Acc. Chem. Res. 1982, 15: 300

Crossref Google Scholar
2e Bailey WF. Patricia JJ. J. Organomet. Chem. 1988, 342: 1

Crossref Google Scholar
2f Wakefield BG. Comprehensive Organometallic Chemistry Vol. 3: Jones DN. Pergamon Press; New York: 1979. p.943

Crossref Google Scholar
2g Wardell JL. Comprehensive Organic Chemistry Vol. 1: Wilkinson G. Pergamon Press; New York: 1982. p.43

Crossref Google Scholar
2h Brandsma L. Veruijsse H. Preparative Polar Organometallic Chemistry I Springer Verlag; Berlin: 1987.

Crossref Google Scholar
2i Slocum DW. Metal-Halogen Exchange Metalations (M-X) of Aryl and Heteroaryl Ring Systems Using Alkyllithiums, In FMC Lithium Link, Winter 1993 FMC Corporation; FMC Lithium Division: 2003.

Crossref Google Scholar
2j Bailey WF. Metal-Halogen Exchange (M-X) Involving Aliphatic Substrates Using Organolithiums, In FMC Lithium Link, Spring 1994 FMC Corporation; FMC Lithium Division: 1994.

Crossref Google Scholar
3a Poss AJ. Fluorinations of Organolithium Reagents, In FMC Lithium Link, Summer 2002 FMC Corporation; FMC Lithium Division: 2002.

Crossref Google Scholar
3b A recent article on the use of the selectfluor reagent for the in situ generation of electrophiles has appeared: Syvret RG. Butt KM. Nguyen TP. Bulleck VL. Rieth RD. J. Org. Chem. 2002, 67: 4487

Crossref Google Scholar
4 DeYoung J. Kawa H. Lagow RJ. J. Chem. Soc., Chem. Commun. 1992, 811

Crossref Google Scholar
5 Bensoam J. Mathey F. Tetrahedron Lett. 1977, 2797

Crossref Google Scholar
6 Schuetz RD. Taft DD. O’Brien JP. Shea JL. Monk HM. J. Org. Chem. 1963, 28: 1420

Google Scholar
7 Schlosser M. Heinz G. Chem. Ber. 1969, 102: 1944

Crossref Google Scholar
8 Peet NP. McCarthy JR. Sunder S. McCowan J. Synth. Commun. 1986, 16: 1551

Crossref Google Scholar
9 Seitz DE. Blaszczak LC. Synth. Commun. 1988, 18: 2353

Crossref Google Scholar
10 Banks RE. Du Boisson RA. Tsiliopoulos E. J. Fluorine Chem. 1986, 32: 461

Crossref Google Scholar
11 Barnette WE. J. Am. Chem. Soc. 1984, 106: 452

Crossref Google Scholar
12 Differding E. Ofner H. Synlett 1991, 187

Article in Thieme Connect Google Scholar
13 Zajc B. J. Org. Chem. 1999, 64: 1902

Crossref Google Scholar
14 Barnes KD. Hu Y. Hunt DA. Synth. Commun. 1994, 24: 1749

Crossref Google Scholar
15 Tagat JR. McCombie SW. Nazareno DV. Boyle CD. Kozlowski JA. Chackalamannil S. Josien H. Wang Y. Zhou G. J. Org. Chem. 2002, 67: 1171

Crossref Google Scholar
16 Nie J. Kirk KL. J. Fluorine Chem. 1995, 74: 297

Crossref Google Scholar
17 Davis FA. Han W. Tetrahedron Lett. 1991, 32: 1631

Crossref Google Scholar
18 Snieckus V. Beaulieu F. Mohri K. Han W. Murphy CK. Davis FA. Tetrahedron Lett. 1994, 35: 3465

Crossref Google Scholar
19 Davis FA. Han W. Murphy CK. J. Org. Chem. 1995, 60: 4730

Crossref Google Scholar
20 Hayashi H. Sonoda H. Fukumura K. Nagata T. J. Chem. Soc., Chem. Commun. 2002, 1618

Google Scholar
21 Boltze KH. Dell HD. Justus Liebigs Ann. Chem. 1967, 709: 63

Crossref Google Scholar
22 Brown JM. Woodward S. J. Org. Chem. 1991, 56: 6803

Crossref Google Scholar
23 Slocum DW. Gierer PL. J. Org. Chem. 1976, 41: 3668

Crossref Google Scholar
24 Ketcha DM. Lieurance BA. Homan DFJ. Gribble GW. J. Org. Chem. 1989, 54: 4350

Crossref Google Scholar
25 Deng S. Taunton J. Org. Lett. 2005, 7: 299

Crossref Google Scholar
26 Vedso P. Begtrup M. J. Org. Chem. 1995, 60: 4995

Crossref Google Scholar
27 Gros P. Louerat F. Fort Y. Org. Lett. 2002, 4: 1759

Crossref Google Scholar
28 Chauder B. Larkin A. Snieckus V. Org. Lett. 2002, 4: 815

Crossref Google Scholar
29 Mani NS. Jablonowski JA. Jones TK. J. Org. Chem. 2004, 69: 8115

Crossref Google Scholar
30 Mathieu J. Gros P. Fort Y. J. Chem Soc., Chem. Commun. 2000, 951

Google Scholar
31 Gros P. Younes-Millot CB. Fort Y. Tetrahedron Lett. 2000, 41: 303

Crossref Google Scholar
32 Havez S. Begtrup M. Vedso P. Andersen K. Ruhland T. J. Org. Chem. 1998, 63: 7418

Crossref Google Scholar
33 Eriksen BL. Vedso P. Begtrup M. J. Org. Chem. 2001, 66: 8344

Crossref Google Scholar
34 Gohier F. Mortier J. J. Org. Chem. 2003, 68: 2030

Crossref Google Scholar
35 Moyroud J. Guesnet J.-L. Bennetau B. Mortier J. Tetrahedron Lett. 1995, 36: 881

Crossref Google Scholar
36 Mongin F. Trécourt F. Gervais B. Mongin O. Quéguiner G. J. Org. Chem. 2002, 67: 3272

Crossref Google Scholar
37 Trécourt F. Gervais B. Mallet M. Quéguiner G. J. Org. Chem. 1996, 61: 1673

Google Scholar
38 Stevens RV. Bisacchi GS. J. Org. Chem. 1982, 47: 2393

Crossref Google Scholar
39 Wipf P. Jung J.-K. J. Org. Chem. 2000, 65: 6319

Crossref PubMed Google Scholar
40 Zhu SS. Cefalo DR. La DS. Jamieson JY. Davis WM. Hoveyda AH. Schrock RR. J. Am. Chem. Soc. 1999, 121: 8251

Google Scholar
41 Cuevas J.-C. Patil P. Snieckus V. Tetrahedron Lett. 1989, 30: 5841

Crossref Google Scholar
42 Cram DJ. Carmack BA. deGrandpre MP. Lein GM. Goldberg I. Knobler CB. Maverick EF. Trueblood KN. J. Am. Chem. Soc. 1987, 109: 7068

Crossref Google Scholar
43 Stangeland EL. Sammakia T. J. Org. Chem. 2004, 69: 2381

Crossref PubMed Google Scholar
44 Mallet M. J. Organomet. Chem. 1991, 406: 49

Crossref Google Scholar
45 Trécourt F. Mallet M. Marsais F. Quéguiner G. J. Org. Chem. 1988, 53: 1367

Crossref PubMed Google Scholar
46 Taylor EC. Vogel DE. J. Org. Chem. 1985, 50: 1002

Crossref Google Scholar
47 Bonfiglio JN. J. Org. Chem. 1986, 51: 2833

Google Scholar
48 Carretero JC. Ruano JLG. Vicioso M. Tetrahedron 1992, 48: 7373

Crossref Google Scholar
49 Kawase T. Asai N. Ogawa T. Oda M. J. Chem. Soc., Chem. Commun. 1990, 339

Crossref Google Scholar
50 Ooi T. Takahashi M. Yamada M. Tayama E. Omoto K. Maruoka K. J. Am. Chem. Soc. 2004, 126: 1150

Crossref Google Scholar
51 Posner GH. Canella KA. J. Am. Chem. Soc. 1985, 107: 2571

Crossref Google Scholar
52 Milburn C. Milburn RR. Snieckus V. Org. Lett. 2005, 7: 629

Crossref Google Scholar
53 Hartung CG. Fecher A. Chapell B. Snieckus V. Org. Lett. 2003, 5: 1899

Crossref Google Scholar
54 Miah MAI. Snieckus V. J. Org. Chem. 1985, 50: 5438

Crossref Google Scholar
55 Stanetty P. Schnürch M. Mereiter K. Mihovilovic D. J. Org. Chem. 2005, 70: 567

Crossref PubMed Google Scholar
56 Finkelstein BL. J. Org. Chem. 1992, 57: 5538

Crossref Google Scholar
57 Lampe JW. Hughes PF. Biggers CK. Smith SH. Hu H. J. Org. Chem. 1994, 59: 5147

Crossref Google Scholar
58 Li C. Lobkovsky E. Porco JA. J. Am. Chem. Soc. 2000, 122: 10484

Crossref Google Scholar
59 Gohier F. Castanet A.-S. Mortier J. J. Org. Chem. 2005, 70: 1501

Crossref Google Scholar
60 Tilly D. Samanta SS. De A. Castanet A.-S. Mortier J. Org. Lett. 2005, 7: 827

Crossref Google Scholar
61 Wu TR. Shen L. Chong JM. Org. Lett. 2004, 6: 2701

Crossref Google Scholar
62 Trost BM. Saulnier MG. Tetrahedron 1985, 26: 123

Crossref Google Scholar
63 Szumigala RH. Devine PN. Gauthier DR. Volante RP. J. Org. Chem. 2004, 69: 566

Crossref Google Scholar
64 Iwao M. Iihama T. Mahalanabis KK. Perrier H. Snieckus V. J. Org. Chem. 1989, 54: 24

Crossref Google Scholar
65 Kelly TR. Xie RL. J. Org. Chem. 1998, 63: 8045

Crossref Google Scholar
66 Kowalik J. Tolbert LM. J. Org. Chem. 2001, 66: 3229

Crossref Google Scholar
67 Schlosser M. Desponds O. Tetrahedron 1994, 50: 5881

Crossref Google Scholar
68 Marsais F. Cronnier A. Trécourt F. Quéguiner G. J. Org. Chem. 1987, 52: 1133

Crossref Google Scholar
69 Holden KG. Mattson MN. Cha KH. Rapoport H. J. Org. Chem. 2002, 67: 5913

Crossref Google Scholar
70 Uchiyama M. Miyoshi T. Kajihara Y. Sakamoto T. Otani Y. Ohwada T. Kondo Y. J. Am. Chem. Soc. 2002, 124: 8514

Crossref PubMed Google Scholar
71 Comins DL. Nolan JM. Org. Lett. 2001, 3: 4255

Crossref Google Scholar
72 Sammakia T. Stangeland EL. Whitcomb MC. Org. Lett. 2002, 4: 2385

Crossref Google Scholar
73 Lucas NT. Notaras EGA. Petrie S. Stranger R. Humphrey MG. Organometallics 2003, 22: 708

Crossref Google Scholar
74 Khaldi M. Chrétien F. Chapleur Y. Bull. Soc. Chim. Fr. 1996, 133: 7

Google Scholar
75 Dijkstra HP. Kruithof CA. Ronde N. van de Coevering R. Ramón DJ. Vogt D. van Klink GPM. van Koten G. J. Org. Chem. 2003, 68: 675

Crossref Google Scholar
76 Cammidge AN. Crépy KVL. J. Org. Chem. 2003, 68: 6832

Crossref Google Scholar
77 Pletnev AA. Tian Q. Larock RC. J. Org. Chem. 2002, 67: 9276

Crossref PubMed Google Scholar
78 MacNeil SL. Familoni OB. Snieckus V. J. Org. Chem. 2001, 66: 3662

Crossref Google Scholar
79 James CA. Snieckus V. Tetrahedron Lett. 1997, 38: 8149

Crossref Google Scholar
80 Lewis A. Stefanuti I. Swain SA. Smith SA. Taylor RJK. Org. Biomol. Chem. 2003, 1: 104

Crossref PubMed Google Scholar
81 Schroeder DR. Stermitz FR. Tetrahedron 1985, 41: 4309

Crossref Google Scholar
82 Grunewald GL. Arrington HS. Bartlett WJ. Reitz TJ. Sall DJ. J. Med. Chem. 1986, 29: 1972

Crossref Google Scholar
83 Zhang YC. Tour JM. J. Am. Chem. Soc. 1999, 121: 8783

Crossref Google Scholar
84 Zhang W. Luo Z. Chen CH.-T. Curran DP. J. Am. Chem. Soc. 2002, 124: 10443

Crossref Google Scholar
85 Strat FL. Harrowven DC. Maddaluno J. J. Org. Chem. 2005, 70: 489

Crossref Google Scholar
86 Kaae BH. Krogsgaard-Larsen P. Johansen TN. J. Org. Chem. 2004, 69: 1401

Crossref Google Scholar
87 Tovar JD. Rose A. Swager TM. J. Am. Chem. Soc. 2002, 124: 7762

Crossref Google Scholar
88 Plé N. Turck A. Couture K. Quéguiner G. Tetrahedron 1994, 34: 10299

Google Scholar
89 Feldman KS. Eastman KJ. Lessene G. Org. Lett. 2002, 4: 3525

Crossref Google Scholar
90 Turck A. Trohay D. Mojovic L. Plé N. Quéguiner G. J. Organomet. Chem. 1991, 412: 301

Crossref Google Scholar
91 Hanson RN. Tonnesen GL. McLaughlin WH. Bloomer WD. Seitz DE. J. Labelled Cmpd. Radiopharm. 1981, 18: 128

Google Scholar
92 Bennacef I. Tymciu S. Dhilly M. Mongin F. Quéguiner G. Lasne M.-C. Barré L. Perrio C. J. Org. Chem. 2004, 69: 2622

Crossref Google Scholar
93 Winkle MR. Ronald RC. J. Org. Chem. 1982, 47: 2101

Google Scholar
94 Ronald RC. Winkle MR. Tetrahedron 1983, 39: 2031

Crossref Google Scholar
95 Boger DL. Garbaccio RM. J. Org. Chem. 1999, 64: 8350

Crossref Google Scholar
96 Dumez E. Snaith JS. Jackson RFW. McElroy AB. Overington J. Wythes MJ. Withka JM. McLellan TJ. J. Org. Chem. 2002, 67: 4882

Crossref Google Scholar
97 Spangler LA. Tetrahedron Lett. 1996, 37: 3639

Crossref Google Scholar
98 Lizos DE. Murphy JA. Org. Biomol. Chem. 2003, 1: 117

Crossref Google Scholar
99 Burke BJ. Overman LE. J. Am. Chem. Soc. 2004, 126: 16820

Crossref Google Scholar
100 Spivey AC. Turner DJ. Turner ML. Yeates S. Org. Lett. 2002, 4: 1899

Crossref PubMed Google Scholar
101 Qui L. Qi J. Pai C.-C. Chan S. Zhou Z. Choi MCK. Chan ASC. Org. Lett. 2002, 4: 4599

Crossref Google Scholar
102 Parker KA. Koziski KA. J. Org. Chem. 1987, 52: 674

Crossref Google Scholar
103 Meyer N. Seebach D. Chem. Ber. 1980, 113: 1304

Crossref Google Scholar
104 Meyers AI. Gabel RA. J. Org. Chem. 1982, 47: 2633

Crossref Google Scholar
105 Harvey RG. Aboshkara E. Pataki J. Tetrahedron 1997, 53: 15947

Crossref Google Scholar
106 Hawthorne MF. J. Org. Chem. 1957, 1001

Google Scholar
107 Ladd DL. Weinstock J. J. Org. Chem. 1981, 46: 203

Crossref Google Scholar
108 Adejare A. Miller DD. Tetrahedron Lett. 1984, 25: 5597

Crossref Google Scholar
109 Hoffmann RW. Ditrich K. Synthesis 1983, 107

Article in Thieme Connect Google Scholar
110 Chen GT. King M. Gusovsky F. Creveling CR. Daly JW. Chen B.-H. Nie J.-Y. Kirk KL. J. Med. Chem. 1993, 36: 3947

Crossref Google Scholar
111 Nerdinger S. Kendall C. Marchhart R. Riebel P. Johnson MR. Yin C.-F. Eltis LD. Snieckus V. J. Chem. Soc., Chem. Commun. 1999, 2259

Google Scholar
112 Beak P. Brown RA. J. Org. Chem. 1982, 47: 34

Crossref Google Scholar
113 Laliberté D. Maris T. Wuest JD. J. Org. Chem. 2004, 69: 1776

Crossref PubMed Google Scholar
114 Krizan TD. Martin JC. J. Am. Chem. Soc. 1983, 105: 6155

Crossref Google Scholar
115 Castagnetti E. Schlosser M. Eur. J. Org. Chem. 2001, 691

Crossref Google Scholar
116 Vyvyan JR. Loitz C. Looper RE. Mattingly CS. Peterson EA. Staben ST. J. Org. Chem. 2004, 69: 2461

Crossref PubMed Google Scholar
117 Stanetty P. Krumpak B. Emerschitz T. Mereiter K. Tetrahedron 1997, 53: 3615

Crossref Google Scholar
118 Harvey RG. Cortez C. Ananthanarayan TP. Schmolka S. J. Org. Chem. 1988, 53: 3936

Crossref Google Scholar
119 Kumazawa K. Ishihara K. Yamamoto H. Org. Lett. 2004, 6: 2551

Crossref Google Scholar
120 Buck P. Köbrich G. Tetrahedron Lett. 1967, 1563

Crossref Google Scholar
121 Wikstrőm H. Elebring T. Hallnemo G. Andersson B. Svensson K. Carlsson A. Rollema H. J. Med. Chem. 1988, 31: 1080

Crossref Google Scholar
122 Braddock DC. MacGilp ID. Perry BG. J. Org. Chem. 2002, 67: 8679

Crossref PubMed Google Scholar
123 Wijtmans M. Pratt DA. Brinkhorst J. Serwa R. Valgimigli L. Pedulli GF. Porter NA. J. Org. Chem. 2004, 69: 9215

Crossref Google Scholar
124 Taddei M. Ricci A. Synthesis 1986, 82: 633

Article in Thieme Connect Google Scholar
125 Sengupta S. Snieckus V. Tetrahedron Lett. 1990, 31: 4267

Crossref Google Scholar
126 Hutchings RH. Meyers AI. J. Org. Chem. 1996, 61: 1004

Crossref Google Scholar
127 Sato R. Ohyama T. Ogawa S. Heterocycles 1995, 41: 893

Crossref Google Scholar
128 Ham J. Yang I. Kang H. J. Org. Chem. 2004, 69: 3236

Crossref Google Scholar
129 Flatt AK. Yao Y. Maya F. Tour JM. J. Org. Chem. 2004, 69: 1752

Crossref Google Scholar
130 Chen LS. Chen GJ. Tamborski C. J. Org. Chem. 1983, 251: 139

Crossref Google Scholar
131 Wipf P. Ribe S. J. Org. Chem. 1998, 63: 6454

Crossref Google Scholar
132 Stanetty P. Koller H. Mihovilovic M. J. Org. Chem. 1992, 57: 6833

Crossref Google Scholar
133 Coll G. Morey J. Costa A. Saá JM. J. Org. Chem. 1988, 53: 5345

Crossref Google Scholar
134 Choppin S. Gros P. Fort Y. Eur. J. Org. Chem. 2001, 603

Crossref Google Scholar
135 Gros P. Fort Y. Caubère P. J. Chem. Soc., Perkin Trans. 1 1997, 3597

Crossref Google Scholar
136 Doadt EG. Snieckus V. Tetrahedron Lett. 1985, 26: 1149

Crossref Google Scholar
137 Levacher V. Eriksen BL. Begtrup M. Dupas G. Quéguiner G. Duflos J. Bourguignon J. Tetrahedron Lett. 1999, 40: 1665

Crossref Google Scholar
138 Gronowitz S. Szabó KJ. Hassan MA. J. Org. Chem. 1992, 57: 4552

Crossref Google Scholar
139 Kayaleh NE. Gupta RC. Johnson F. J. Org. Chem. 2000, 65: 4515

Crossref Google Scholar
140 Carpenter AJ. Chadwick DJ. J. Org. Chem. 1985, 50: 4362

Crossref Google Scholar
141 Stanetty P. Krumpak B. Rodler IK. J. Chem. Res., Synop. 1995, 342

Google Scholar
142 Godard A. Jacquelin J.-M. Quéguiner G. J. Organomet. Chem. 1988, 354: 273

Crossref Google Scholar
143 Turner JA. J. Org. Chem. 1983, 48: 3401

Crossref Google Scholar
144 Fuhrer W. Gschwend HW. J. Org. Chem. 1979, 44: 1133

Crossref Google Scholar
145 Pozharskii AF. Ryabtsova OV. Ozeryanskii VA. Degtyarev AV. Kazheva ON. Alexandrov GG. Dyachenko OA. J. Org. Chem. 2003, 68: 10109

Crossref Google Scholar
146 Mortier J. Moyroud J. Bennetau B. Cain PA. J. Org. Chem. 1994, 59: 4042

Google Scholar
147 Clark RD. Caroon JM. J. Org. Chem. 1982, 47: 2804

Crossref Google Scholar
148 Pradhan TK. Ghosh SC. De A. Arkivoc 2003, (ix): 158

Google Scholar
149 Mills RJ. Snieckus V. J. Org. Chem. 1983, 48: 1565

Crossref Google Scholar
150 Martineau D. Gros P. Fort Y. J. Org. Chem. 2004, 69: 7914

Crossref Google Scholar
151 Cabiddu S. Fattuoni C. Floris C. Gelli G. Melis S. Sotgiu F. Tetrahedron 1990, 46: 861

Crossref Google Scholar
152 Cabiddu S. Contini L. Fattuoni C. Floris C. Gelli G. Tetrahedron 1991, 47: 9279

Crossref Google Scholar
153 Kozaki M. Yonezawa Y. Okada K. Org. Lett. 2002, 4: 4535

Crossref Google Scholar
154 Clayden J. Julia M. J. Chem. Soc., Chem. Commun. 1993, 1682

Crossref Google Scholar
155 Lipshutz BH. Huff B. Hagan W. Tetrahedron Lett. 1988, 29: 3411

Crossref Google Scholar
156 Feldman KS. Skoumbourdis AP. Org. Lett. 2005, 7: 929

Crossref Google Scholar
157 Liu W. Wise DS. Townsend LB. J. Org. Chem. 2001, 66: 4783

Crossref Google Scholar
158 Fukuda T. Mine Y. Iwao M. Tetrahedron 2001, 57: 975

Crossref Google Scholar
159 Katritzky AR. Lue P. Chen Y.-X. J. Org. Chem. 1990, 55: 3688

Crossref Google Scholar
160 Kraus GA. Kim J. J. Org. Chem. 2002, 67: 2358

Crossref Google Scholar
161 Katritzky AR. Lue P. J. Org. Chem. 1990, 55: 74

Crossref Google Scholar
162 Muchowski JM. Venuti MC. J. Org. Chem. 1980, 45: 4798

Crossref Google Scholar
163 Gribble GW. Saulnier MG. Tetrahedron Lett. 1980, 21: 4137

Crossref Google Scholar
164 Beaulieu F. Snieckus V. Synthesis 1992, 112

Article in Thieme Connect Google Scholar
165 Song JJ. Yee NK. Tan Z. Xu J. Kapadia SR. Senanayake CH. Org. Lett. 2004, 6: 4905

Crossref Google Scholar
166 Sotgui G. Zambianchi M. Barbarella G. Aruffo F. Cipriani F. Ventola A. J. Org. Chem. 2003, 68: 1512

Crossref Google Scholar
167 Yamazaki D. Nishinaga T. Komatsu K. Org. Lett. 2004, 6: 4179

Crossref Google Scholar
168 Lukács G. Porcs-Makkay M. Simig G. Tetrahedron Lett. 2003, 44: 3211

Crossref Google Scholar
169 Selnick HG. Bourgeois ML. Butcher JW. Radzilowski EM. Tetrahedron Lett. 1993, 34: 2043

Crossref Google Scholar
170 Beaulieu F. Snieckus V. J. Org. Chem. 1994, 59: 6508

Crossref Google Scholar
171 Smith K. Hou D. J. Org. Chem. 1996, 61: 1530

Crossref Google Scholar
172 Figuly GD. Martin JC. J. Org. Chem. 1980, 45: 3729

Crossref Google Scholar
173 Smith K. Lindsay CM. Pritchard GJ. J. Am. Chem. Soc. 1989, 111: 665

Crossref Google Scholar
174 Mugesh G. Singh HB. Acc. Chem. Res. 2002, 35: 226

Crossref PubMed Google Scholar
175 Wilson SR. Zucker PA. Huang R.-RC. Spector A. J. Am. Chem. Soc. 1989, 111: 5936

Crossref Google Scholar
176 Brennan NK. Donnelly DJ. Detty MR. J. Org. Chem. 2003, 68: 3344

Crossref Google Scholar
177 Mugesh G. Panda A. Kumar S. Apte SD. Singh HB. Butcher RJ. Organometallics 2002, 21: 884

Crossref Google Scholar
178 Mugesh G. Panda A. Singh HB. Punekar NS. Butcher RJ. J. Am. Chem. Soc. 2001, 123: 839

Crossref Google Scholar
179 Zade SS. Panda S. Singh HB. Sunoj RB. Butcher RJ. J. Org. Chem. 2005, 70: 3693

Crossref Google Scholar
180 Kumar S. Kandasamy K. Singh HB. Wolmershäuser G. Butcher RJ. Organometallics 2004, 23: 4199

Crossref Google Scholar
181 Chiang L.-Y. Meinwald J. Tetrahedron Lett. 1980, 21: 4565

Crossref Google Scholar
182 Tiecco M. Testaferri L. Santi C. Tomassini C. Marini F. Bagnoli L. Temperini A. Chem.-Eur. J. 2002, 8: 1118

Google Scholar
183 Tiecco M. Testaferri L. Santi C. Tomassini C. Bohini R. Marini F. Bagnoli L. Temperini A. Org. Lett. 2004, 6: 4751

Crossref Google Scholar
184 Klapötke TM. Krumm B. Polborn K. J. Am. Chem. Soc. 2004, 126: 710

Crossref Google Scholar
185 Panda A. Mugesh G. Singh HB. Butcher RJ. Organometallics 1999, 18: 1986

Crossref Google Scholar
186 Mogemark M. Gustafsson L. Bengtsson C. Elofsson M. Kihlberg J. Org. Lett. 2004, 6: 4885

Crossref Google Scholar
187 Hanekamp JC. Klusener PAA. Brandsma L. Synth. Commun. 1989, 19: 2691

Crossref Google Scholar
188 Kojima T. Tanaka K. Ishida T. Nogami T. J. Org. Chem. 2004, 69: 9319

Crossref Google Scholar
189 Hope EG. Kemmitt T. Levason W. Organometallics 1987, 6: 206

Crossref Google Scholar
190 Menon SC. Singh HB. Jasinski JM. Jasinski JP. Butcher RJ. Organometallics 1996, 15: 1707

Crossref Google Scholar