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Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction

Chao Pei, Zhen Yang and Rene M. Koenigs*

*RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany, Email:

C. Pei, Z. Yang, R. M. Koenigs, Org. Lett., 2020, 22, 7300-7304.

DOI: 10.1021/acs.orglett.0c02638

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A Pd-catalyzed reaction of vinyl bromides and trifluoromethylated diazoalkanes provides trifluoromethylated, tetrasubstituted allenes in very good yield under mild reaction conditions. This reaction proceeds via oxidative addition of Pd(0) to the vinyl bromide followed by base-promoted reductive elimination. An acid catalyzed cyclization of the allenes gives trifluoromethylated indenes.

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proposed mechanism

Key Words

trifluoromethyl allenes, allenes

ID: J54-Y2020