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Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes

Yu Ma, Bhoomireddy Rajendra Prasad Reddy and Xihe Bi*

*Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email:

Y. Ma, B. R. P. Reddy, X. Bi, Org. Lett., 2019, 21, 9860-9863.

DOI: 10.1021/acs.orglett.9b03740

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A gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids - including alkylboronic acids - is operationally simple, free of transition metals, and suitable for a broad range of substrates. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.

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Key Words

vinylation (alkanes, arenes), gem-difluoroalkenes

ID: J54-Y2019