Intermolecular σ-Bond Cross-Exchange Reaction between Cyclopropenones and (Benzo)silacyclobutanes: Straightforward Access towards Sila(benzo)cycloheptenones

Wen-Tao Zhao; Fang Gao; Dongbing Zhao

doi:10.1002/anie.201803156

Intermolecular σ-Bond Cross-Exchange Reaction between Cyclopropenones and (Benzo)silacyclobutanes: Straightforward Access towards Sila(benzo)cycloheptenones

Angew Chem Int Ed Engl. 2018 May 22;57(21):6329-6332. doi: 10.1002/anie.201803156. Epub 2018 Apr 25.

Authors

Wen-Tao Zhao¹, Fang Gao¹, Dongbing Zhao¹

Affiliation

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.

PMID: 29645332
DOI: 10.1002/anie.201803156

Abstract

Described herein is the first intermolecular σ-bond exchange reaction between the C-C bond of cyclopropenones and C-Si bond of (benzo)silacyclobutanes and it proceeds smoothly by treatment with either 1 mol % of a palladium or 2 mol % of a nickel catalyst. This reaction constitutes an unprecedented route for the synthesis of various sila(benzo)suberones. And it is also the first example of a σ-bond exchange reaction involving cyclopropenones.

Keywords: heterocycles; palladium; ring expansion; silanes; strained molecules.

Publication types

Research Support, Non-U.S. Gov't