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J Am Chem Soc. 2015 Dec 23;137(50):15648-51. doi: 10.1021/jacs.5b10971. Epub 2015 Dec 10.

Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes.

Journal of the American Chemical Society

Chaohuang Chen, Pinhong Chen, Guosheng Liu

Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

PMID: 26636720 DOI: 10.1021/jacs.5b10971

Abstract

The first catalytic trifluoromethoxylation of unactivated alkenes has been developed, in which Pd(CH3CN)2Cl2 was used as catalyst, AgOCF3 as trifluoromethoxide source, and Selectfluor-BF4 as oxidant. A variety of 3-OCF3 substituted piperidines were selectively obtained in good yields. Direct evidence was provided to address the facile reductive elimination of Pd(IV)-OCF3 complex to form sp(3) C-OCF3 bond.

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