Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol?

Chemical Science Pub Date: 2021-06-07 DOI: 10.1039/D1SC02625A

Abstract

Methanol is an abundant and renewable chemical raw material, but its use as a C1 source in C–C bond coupling reactions still constitutes a big challenge, and the known methods are limited to the use of expensive and noble metal catalysts such as Ru, Rh and Ir. We herein report nickel-catalyzed direct coupling of alkynes and methanol, providing direct access to valuable allylic alcohols in good yields and excellent chemo- and regioselectivity. The approach features a broad substrate scope and high atom-, step- and redox-economy. Moreover, this method was successfully extended to the synthesis of [5,6]-bicyclic hemiacetals through a cascade cyclization reaction of alkynones and methanol.

Graphical abstract: Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol
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