Metalation reactions. XXIV. Metalation of (vinylthio)benzene

Add time:08/28/2019    Source:sciencedirect.com

The addition of organolithium compounds to (vinylthio)benzene (1) and then an electrophilic quenching followed by a further metalation/electrophilic quenching is a general method to prepare in one pot (alkylthio)benzenes ortho, alpha-substituted with equal or different groups. The direct dimetalation of 1 affords the ortho, alpha-dilithiated species 15 besides other by-products. Starting from 15 it is possible to obtain in one step ortho, alpha-substituted (vinylthio)benzenes and heterocyclic compounds.

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