The Journal of organic chemistry

Fast and regioselective Heck couplings with N-acyl-N-vinylamine derivatives

AL Hansen, T Skrydstrup

Index: Hansen, Anders Lindhardt; Skrydstrup, Troels Journal of Organic Chemistry, 2005 , vol. 70, # 15 p. 5997 - 6003

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Citation Number: 62

Abstract

Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N- alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol% of Pd2 (dba) 3, 3 mol% of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling ...