4.8 Article

CaCl2-Promoted Dehydroxytrifluoromethylselenolation of Alcohols with [Me4N][SeCF3]

Journal

ORGANIC LETTERS
Volume 22, Issue 15, Pages 6016-6020

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02109

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Funding

  1. Wuhan University of Technology
  2. National Natural Science Foundation of China [21602165]
  3. Hundred Talent Program of Hubei Province (China)
  4. Chongqing Research Program of Basic and Frontier Technology [cstc2017jcyjAX0303]

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A direct trifluoromethylselenolation of alcohols with the readily accessible [Me4N][SeCF3] salt has been reported. The reaction is significantly promoted by CaCl2 and proceeds smoothly through unprecedented carbonoselenoate intermediates to form the corresponding alkyl trifluoromethyl selenoethers in good yields. This protocol is also applicable to the late-stage dehydroxytrifluoromethylselenolation of complex alcohols owing to its mildness, good compatibility, high efficiency, and broad functional group tolerance.

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