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Communication | Regular issue | Vol 24, No. 8, 1986, pp.2127-2131
Published online, 1st January, 1970
DOI: 10.3987/R-1986-08-2127
Directed beta-Lithiation of 2-Substituted Indoles — A New Synthetic Route to 2,3-Substituted Indoles

David A. Johnson and Gordon W. Gribble*

*Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03775, U.S.A.

Abstract

Treatment of several N-protected 2-substituted indoles with n-butyllithium at -78°C leads toC-3 lithiation, presumably via coordination with the C-2 substituent. Depending on the exact system, the 3-lithioindole can either be trapped with electrophiles or suffer ring-opening to an alkyne.