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- Title
Nickel-Catalyzed Cyclopropanation with NMe<sub>4</sub>OTf and nBuLi.
- Authors
Künzi, Stefan A.; Sarria Toro, Juan Manuel; den Hartog, Tim; Chen, Peter
- Abstract
Nickel was identified as a catalyst for the cyclopropanation of unactivated olefins by using in situ 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 Additionally, our findings shed light on a report by Franzen and Wittig published in 1960 that had been retracted later owing to irreproducibility, and provide a rational basis for the systematic development of the reaction for preparative purposes as an alternative to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.
- Subjects
CYCLOPROPANATION; NICKEL; CATALYSIS; ALKENES; METHYLENE group; CHEMICAL reactions
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 36, p10670
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201505482