Tetrahedron

Dibromomethane as one-carbon source in organic synthesis: microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine

…, TR Hsu, CY Chen, YH Lin, FJ Chang, CH Hsieh…

Index: Hon, Yung-Son; Hsu, Tzyy-Rong; Chen, Chun-Yan; Lin, Yi-Hui; Chang, Fong-Jong; Hsieh, Cheng-Han; Szu, Ping-Hui Tetrahedron, 2003 , vol. 59, # 9 p. 1509 - 1520

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Citation Number: 42

Abstract

The reactivity of aryl alkyl ketone with a preheated mixture of dibromomethane and diethylamine is poor and gives an α-methylenation product in very low yield even under refluxing condition. It can be accelerated dramatically by microwave irradiation. Under microwave condition, the cyclic 1, 3-dicarbonyls, aryl alkyl ketones, heteroaryl alkyl ketones and acyclic benzyl ketone give α-methylenation products in modest to good yields.