Direct C(sp)-H/Si-H Cross-Coupling via Copper Salts Photocatalysis

Reported herein is the first example of C(sp)-H/Si-H cross-coupling by photocatalysis. In terms of cheap and readily available starting materials, a series of alkynylsilanes are prepared in good to excellent yields upon visible-light irradiation of CuCl and alkynes with silane. The large scale reaction with flow chemistry and late-stage functionalization of natural products shows the potential of the transformation in practical organic synthesis of the alkynylsilanes intermediates.

Automated summary

This paper reports the first example of C(sp)-H/Si-H cross-coupling by photocatalysis. A series of alkynylsilanes are prepared in good to excellent yields using cheap and readily available starting materials and visible-light irradiation of CuCl and alkynes with silane. The potential of this transformation in practical organic synthesis of alkynylsilane intermediates is shown through large scale reactions with flow chemistry and late-stage functionalization of natural products.