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Heck Reaction of 2‑Oxyacrylates with Aryl Bromides: A Common Route to Monoaryl Pyruvates and Ortho Ester-Protected Monoaryl Pyruvates

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posted on 2022-08-03, 19:22 authored by Kiran Matcha, Konstantin Chernichenko, Kévin Jouvin, Suresh Babu Guduguntla, Duc N. Tran, Stephen Bell, Warren Paden, Marek Figlus, Colin Muir, Alain Elliott, Cristina Hernandez Diaz
A palladium-catalyzed Heck reaction between 2-oxyacrylates and aryl bromides was developed, where DavePhos was a unique ligand that efficiently promoted the reaction. The products, 2-oxycinnamates, served as excellent precursors, providing synthetically useful monoaryl pyruvates or ortho ester-protected monoaryl pyruvates depending on the nature of the 2-oxy group. The formation of such ortho esters via alkoxide addition is novel, and computational studies identified a plausible mechanism with an oxyallyl zwitterion as the key intermediate.

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