Oxygen-directed, copper-catalyzed, diastereoselective protosilylation of cyclopropenes
Yueyuan Wang1, Longtao Huang1, Shizhao Xu1
1Central Hospital of Dalian University of Technology, School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024, China. huanglongtao@dlut.edu.cn.
Abstract:
Herein, we report a copper-catalyzed, oxygen-directed protosilylation of cyclopropenes. This method provides a facile approach to access organosilanes bearing a cyclopropyl group with broad functional group tolerance. The key to the success of this process lies in the use of a monodentate N-heterocyclic carbene as the ligand, which leaves a vacant site on the copper center for coordination with the OH or ester group. Preliminary mechanistic studies reveal that the hydroxyl or ester group not only acts as a directing group (DG) but also significantly enhances reactivity.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)