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Sustainable Heck-Matsuda reaction with catalytic amounts of diazonium salts: an experimental and theoretical study.

The palladium-catalyzed Heck-Matsuda reaction with a catalytic amount of an in-situ-generated diazonium salt proceeded under mild and sustainable conditions. The reaction proceeded at room temperature, under base-free conditions, and only generated tBuOH, H(2)O, and N(2) as by-products. Ortho-substituted diazonium salts were more-efficiently coupled to methyl acrylate than their corresponding para isomers, which required the addition of anisole as an additive. In support of these experimental data, we carried out theoretical studies to gain a deeper understanding of these reaction outcomes.