Palladium-Catalyzed Intermolecular Ditrifluoromethoxylation of Unactivated Alkenes: CFO-Palladation Initiated by Pd(IV).

J Am Chem Soc

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Published: January 2018

A novel palladium-catalyzed intermolecular ditrifluoromethoxylation of unactivated alkenes has been developed, using a new electrophilic reagent, Selectfluor, as a strong oxidant, and AgOCF as a trifluoromethoxide source. Preliminary mechanistic studies revealed that the reaction was possibly initiated by Pd(IV) species, and an unusual cis-addition of CFO-Pd(IV) into the double bond leads to the formation of the first C-OCF bond; in addition, the second C-OCF bond was produced through reductive elimination at high-valent palladium center.

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Source
http://dx.doi.org/10.1021/jacs.7b11470DOI Listing

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