Tetrahedron Letters p. 2537 - 2540 (1996)
Update date:2022-08-17
Topics:
Cai, Dongwei
Hughes, David L.
Verhoeven, Thomas R.
Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-bromo-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield.
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