Abstract
Cross-coupling reactions occur on 2,4-dibromothiazole preferentially
at the more electron-deficient 2-position. This fact can be favorably
used to prepare 2-substituted 4-bromothiazoles, which serve as precursors
for 2,4-disubstituted thiazoles. Protocols for regioselective Negishi
and Stille cross-coupling reactions are provided. Alternatively,
the title compound can be metalated in 2-position by a halogen-metal
exchange reaction. As a supplement to the well-established bromine-lithium
exchange, the regioselective bromine-magnesium exchange
reaction is presented.
Key words
catalysis - cross-coupling - heterocycles - palladium - regioselectivity - thiazoles
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