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Chichibabin-Type Direct Alkylation of Pyridyl Alcohols with Alkyl Lithium Reagents

Author:
Jeffrey, Jenna L., Sarpong, Richmond
Source:
Organic letters 2012 v.14 no.21 pp. 5400-5403
ISSN:
1523-7052
Subject:
alcohols, alkylation, chemical structure, lithium, pyridines, regioselectivity
Abstract:
Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation.
Agid:
5784579