Active Metal Tin Promoted Allylation of Imidazoles and Its Derivatives via Unstable N-(Alkoxycarbonyl)azolium Salts

Jing-Yao Zhou; Zhao-Gen Chen; Shi-Hui Wu

doi:10.1055/s-1995-5224

Synlett 1995; 1995(11): 1117-1118
DOI: 10.1055/s-1995-5224

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Active Metal Tin Promoted Allylation of Imidazoles and Its Derivatives via Unstable N-(Alkoxycarbonyl)azolium Salts

Jing-Yao Zhou, Zhao-Gen Chen, Shi-Hui Wu^*

^*Department of Chemistry, Fudan University, Shanghai 200433, China

Abstract

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The active metal tin promoted one-pot reactions of imidazoles with allylic bromides or propargyl bromide in the presence of alkyl chloroformates afforded the corresponding allylation or propargylation products at 2-position in good yields. Under similar conditions, reaction of crotyl bromide exhibited very high regioselectivity favoring γ-adducts. The reaction of thiazole also proceeded in a similar manner.

Active Metal Tin - Allylation - Imidazole - Selectivity

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