期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 25, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202202175
关键词
Carbenes; Cyclopropanation; Cyclopropanols; Organosilanes; Photocatalysis
资金
- National Natural Science Foundation of China [21901191]
- Fundamental Research Funds for the Central Universities
- Wuhan University
In this study, a novel visible-light-induced transition-metal-free cyclopropanation reaction of alkenes was reported. The reaction exhibited high selectivity and was suitable for various alkene substrates, demonstrating its synthetic potential in gram-scale reactions and late-stage functionalization.
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.
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