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

Org Lett

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

Published: December 2019

The synthesis of alkyl -difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by -difluoroolefination of trifluoroacetaldehyde -triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the -difluorovinyl group.

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http://dx.doi.org/10.1021/acs.orglett.9b03740DOI Listing

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