Recyclable Pd(OAc)₂/2P(3-tol)₃/PEG-400 System for Regio- and Stereoselective Addition of Boronic Acids to Ynamides

Abstract

Pd(OAc)₂/2P(3-tol)₃ in poly(ethylene glycol) (PEG-400) is shown to be a highly efficient catalyst for the regio- and stereoselective addition of boronic acids to ynamides. The reaction proceeds smoothly at 70 °C with Na₂CO₃ as base, delivering a variety of (Z)-α,β-disubstituted enamides in good to excellent yields with high regio- and stereoselectivity. The isolation of the crude products can be facilely performed by extraction with diethyl ether and more importantly, the Pd(OAc)₂/2P(3-tol)₃/PEG-400 system could be readily recycled and reused more than six times without any significant loss of its catalytic efficiency.

Key words

palladium - enamides - ynamides - boronic acids - poly(ethylene glycol)

Publication History

Received: 13 July 2024

Accepted after revision: 29 August 2024

Article published online:
25 September 2024

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