By carefully choosing the reaction conditions, we have developed the controllable FeCl- or CuCl-mediated dehydrazinative hydrogenation or chlorination of 3,3-difluoroallyl hydrazines to access α-CFH or α-CFCl styrenes. The current reaction provides for the first time a facile method for the direct and selective synthesis of α-CFH and α-CFCl styrenes starting from the same precursors, which is easy to scale up and displays a broad substrate scope and good functional group tolerance. Moreover, product derivatization experiments demonstrated that the resulting α-CFCl styrenes are practical and versatile building blocks for the diversified synthesis of fluorinated molecules.

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http://dx.doi.org/10.1021/acs.joc.3c00355DOI Listing

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