Issue 19, 2022

Regiodivergent hydrosilylation in the nickel(0)-catalyzed cyclization of 1,6-enynes

Abstract

Transition-metal-catalyzed hydrosilylation is an efficient strategy for the synthesis of valuable organosilanes, while divergent synthetic routes are still a challenge. Herein, we realized the nickel(0)-catalyzed divergent hydrosilylation/cyclization of 1,6-enynes to construct two different types of cyclic organosilanes from the same starting materials. A variety of functionalized 1,6-enynes reacted with silanes to give vinyl silanes or alkyl silanes with excellent regio- and diastereo-selectivity. Moreover, silanol products could also be formed when water was added. Synthetic value and mechanistic studies were also performed.

Graphical abstract: Regiodivergent hydrosilylation in the nickel(0)-catalyzed cyclization of 1,6-enynes

Supplementary files

Article information

Article type
Research Article
Submitted
07 Aug 2022
Accepted
12 Aug 2022
First published
30 Aug 2022

Org. Chem. Front., 2022,9, 5285-5291

Regiodivergent hydrosilylation in the nickel(0)-catalyzed cyclization of 1,6-enynes

D. Bai, R. Cheng, J. Yang, W. Xu, X. Chen and J. Chang, Org. Chem. Front., 2022, 9, 5285 DOI: 10.1039/D2QO01266A

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