Issue 22, 2023

Atom-economical synthesis of bicyclo[3.1.0]hexane silanes by gold-catalyzed Si–H bond insertion reaction of 1,6-enynes with hydrosilanes

Abstract

The gold-catalyzed Si–H bond insertion reaction of 1,6-enynes with hydrosilanes, which proceeds through cyclopropyl gold carbene intermediates, allows the facile, practical, and atom-economical one-step construction of various bicyclo[3.1.0]hexane silanes in moderate to excellent yields (up to 91%) under mild reaction conditions. This reaction can be easily carried out on a gram scale, which illustrates the synthetic practicability of this protocol. Moreover, a gold-catalyzed carbene insertion into Ge–H bonds is reported for the first time.

Graphical abstract: Atom-economical synthesis of bicyclo[3.1.0]hexane silanes by gold-catalyzed Si–H bond insertion reaction of 1,6-enynes with hydrosilanes

Supplementary files

Article information

Article type
Research Article
Submitted
18 Jul 2023
Accepted
02 Oct 2023
First published
04 Oct 2023

Org. Chem. Front., 2023,10, 5705-5709

Atom-economical synthesis of bicyclo[3.1.0]hexane silanes by gold-catalyzed Si–H bond insertion reaction of 1,6-enynes with hydrosilanes

G. Wang, H. Li, Y. Wang, Z. Li, G. Liu and X. Zhao, Org. Chem. Front., 2023, 10, 5705 DOI: 10.1039/D3QO01112G

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