Regioselective Heck couplings of alpha,beta-unsaturated tosylates and mesylates with electron-rich olefins

Abstract

[chemical reaction: see text]. Highly regioselective Heck couplings of alpha,beta-unsaturated tosylate and mesylate derivatives with N-acyl N-vinylamines and vinyl ethers were achieved. Several 2-alkoxy-1,3-dienes and 2-acylamino-1,3-butadienes were synthesized in good yields using 1.5 mol % of Pd2(dba)3, 3 mol % of DPPF, and diisopropylethylamine in dioxane. When working with alpha,beta-unsaturated ketones and esters, this method provides a less costly alternative to similar couplings using a triflate electrophile.