Diastereoselective Transfer of Tri(di)fluoroacetylsilanes-Derived Carbenes to Alkenes
Related Experiment Video
Updated: Sep 27, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Yizhi Zhang1, Gang Zhou1, Xingxing Gong1
1Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072, China.
Abstract:
Stereoselective cyclopropanation reaction of alkenes is usually achieved by metal complexes via singlet-metal-carbene intermediates. However, previous transition-metal-catalyzed cyclopropanation of alkenes with acylsilanes afforded low diastereoselectivity. Herein, we report the first visible-light-induced transition-metal-free cyclopropanation reaction of terminal alkenes with trifluoroacetylsilanes and difluoroacetylsilanes. Both aromatic and aliphatic alkenes as well as electron-deficient alkenes are suitable substrates for the highly cis-selective [2+1] cyclization reaction. A combination of experimental and computational studies identified triplet carbenes as being key intermediates in this transformation. The gram scale reaction and late-stage functionalization demonstrated the synthetic potential of this strategy.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration