Directed Deprotonation−Transmetalation as a Route to Substituted Pyridines
- 21 February 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (6), 835-838
- https://doi.org/10.1021/ol006986z
Abstract
Regioselective C-4 deprotonation of 3-bromopyridine, followed by Li/Zn transmetalation and Pd-mediated coupling processes, provides a flexible entry to 4-substituted and 3,4-disubstituted pyridines. Application of a similar sequence to 2-bromopyridine (with LDA as base) provides 2,3-disubstituted pyridines, but using lithium 2,2,6,6-tetramethylpiperidide (LiTMP) provides access to both the 2,3- and 2,4-disubstituted isomers.Keywords
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