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Synlett 2004(8): 1440-1442
DOI: 10.1055/s-2004-825611
DOI: 10.1055/s-2004-825611
LETTER
© Georg Thieme Verlag Stuttgart · New York
Generation of Bromophenyllithium Reagents from Dibromobenzenes and Addition to Carbonyl and Nitrile Electrophiles
Further Information
Received
25 March 2004
Publication Date:
18 May 2004 (online)
Publication History
Publication Date:
18 May 2004 (online)
Abstract
An evaluation of the mono-lithiation of all three regio-isomers of dibromobenzene using n-butylithium was performed. The resulting aryllithium reagents were added to electrophiles such as ketones, aldehydes, nitriles and amides to afford the desired benzylic alcohols or ketones.
Key words
dibromobenzene - organolithium - halogen-metal exchange - addition - aryllithium
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Knochel P.Dohle W.Gommermann N.Kneisel FF.Kopp F.Korn T.Sapountzis I.Vu VA. Angew. Chem. Int. Ed. 2003, 42: 4302 - 2
Najera C.Sansano JM.Uyus M. Tetrahedron 2003, 59: 9255 - 3
Boymond L.Rottlander M.Cahiez G.Knochel P. Angew. Chem. Int. Ed. 1998, 37: 1701 - 4
Kitagawa K.Inoue A.Shinokubo H.Oshima K. Angew. Chem. Int. Ed. 2000, 39: 2481 - 5
Sell MS.Hanson MV.Rieke RD. Synth. Commun. 1994, 24: 2379 - 6
Gilman H.Langham W.Moore FW. J. Am. Chem. Soc. 1940, 62: 2327 - 7
Chauret N.Guay D.Li C.Day S.Silva J.Blouin M.Ducharme Y.Yergey JA.Nicoll-Griffith DA. Bioorg. Med. Chem. Lett. 2002, 12: 2149 - 8
Al-Dulayymi A.Li X.Neuenschwander M. Helv. Chim. Acta 2000, 83: 1633 - 9
Reynolds DW.Cassidy PE.Johnson CG.Cameron ML. J. Org. Chem. 1990, 55: 4448 - 10
McCague R.Leclercq G.Legros N.Goodman J.Blackburn M.Jarman M.Foster AB. J. Med. Chem. 1998, 32: 2527 - 11
Gribble GW.Nataitis CF. Tetrahedron Lett. 1985, 26: 6023 - 12
Rajca A. J. Org. Chem. 1991, 56: 2557 - 13
Klusener PAA.Hanekamp JC.Brandsma L.von Ragué Schleyer P. J. Org. Chem. 1990, 55: 1311 - 14
Leroux F.Schlosser M. Angew. Chem. Int. Ed. 2002, 41: 4272 - 15
Wittig G. Naturwissenschaften 1942, 30: 969 - 16
Chen LS.Chen GJ.Tamborski C. J. Organomet. Chem. 1980, 193: 283 - 17
Gilman H.Gorsich RD. J. Am. Chem. Soc. 1956, 78: 2217 - 18
Martin R.Romea P.Tey C.Urpf F.Vilarrasa J. Synlett 1997, 1414 - 19
Nahm S.Weinreb SM. Tetrahedron Lett. 1981, 22: 3815