Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 36, Pages 10670-10674Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505482
Keywords
carbenes; cyclopropanation; nickel; ylides
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Funding
- ETH Zurich
- Swiss National Science Foundation
- European Union [PIEF-GA-2010-275400]
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Nickel was identified as a catalyst for the cyclopropanation of unactivated olefins by using insitu generated lithiomethyl trimethylammonium triflate as a methylene donor. A mechanistic hypothesis is proposed in which the generation of a reactive nickel carbene explains several interesting observations. Additionally, our findings shed light on a report by Franzen and Wittig published in 1960 that had been retracted later owing to irreproducibility, and provide a rational basis for the systematic development of the reaction for preparative purposes as an alternative to diazomethane or Simmons-Smith conditions.
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