REACTION OF ORGANOLITHIUMS WITH FLUORO-N,N-DIALLYLANILINES - A BENZYNE-MEDIATED ANIONIC CASCADE LEADING TO 3,4-DISUBSTITUTED INDOLINES

Authors
BAILEY WF CARSON MW
Citation
Wf. Bailey et Mw. Carson, REACTION OF ORGANOLITHIUMS WITH FLUORO-N,N-DIALLYLANILINES - A BENZYNE-MEDIATED ANIONIC CASCADE LEADING TO 3,4-DISUBSTITUTED INDOLINES, Tetrahedron letters, 38(8), 1997, pp. 1329-1332
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
8
Year of publication
1997
Pages
1329 - 1332
Database
ISI
SICI code
0040-4039(1997)38:8<1329:ROOWF->2.0.ZU;2-1
Abstract
Regioselective ortho-lithiation of either 2-fluoro- (2) or 3-fluoro-N, N-diallylaniline (3) initiates an anionic cascade leading to an N-ally l-3,4-disubstitutedindoline. The transformation involves loss of LiF f rom the ortho-lithiated species, regioselective intermolecular additio n of the organolithium to the benzyne intermediate, and cyclization of the resulting [6-substituted-2-(N,N-diallylamino)phenyl]lithium. (C) 1997 Elsevier Science Ltd.