4.5 Article

Structure of Bis(trifluoromethyl)cuprate and Its Role in Trifluoromethylation Reactions

Journal

ORGANOMETALLICS
Volume 27, Issue 23, Pages 6233-6235

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/om800794m

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Funding

  1. Office of Basic Energy Sciences of the U.S. Department of Energy [DEFG02-07ER15885]

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An equilibrium between [(SIMes)Cu-CF3] (1, SIMes = 1,3-dimesitylimidazolin-2-ylidene) and the cuprate salt [(SIMeS)(2)Cu][(CF3)(2)Cu] (2) was Observed. Synthetic methods to prepare and isolate 2 are reported. Trifluoromethylations using equilibrium Mixtures of 1 and 2 occur readily for aryl iodides and even occur for aryl bromides at 90 degrees C. Kinetic data suggest the cuprate form does not play a significant role in trifluoromethylations using N-heterocyclic carbene complexes of copper.

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