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Directed deprotonation-transmetalation as a route to substituted pyridines
G Karig1, J A Spencer, T Gallagher
1School of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
Organic Letters
|March 27, 2001
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.