期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 47, 页码 16959-16965出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908994
关键词
computational analysis; cyclopropanation; hypervalent iodine; iodonium ylides; LED photochemistry
资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- University of Waterloo
- Initiative of Excellence (IdEx) of the University of Bordeaux
- Compute Canada
A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures of alkenes and beta-dicarbonyl-derived iodonium ylides are irradiated with light from blue LEDs. This metal-free synthesis gives cyclopropanes in yields up to 96 %, is operative with cyclic and acyclic ylides, and proceeds with a variety of electronically-diverse alkenes. Computational analysis explains the high selectivity observed, which derives from exclusive HOMO to LUMO excitation, instead of free carbene generation. The procedure is operationally simple, uses no photocatalyst, and provides access in one step to important building blocks for complex molecule synthesis.
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