Sequential One-Pot Transformation to R-CF-Embedded 1,5-Diketones Enabled by Nickel: Access to 4-Perfluoroalkylpyridines.

Org Lett

Laboratory of Catalysis and Organic Synthesis, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India.

Published: November 2024

Herein, we have demonstrated the application of bench-stable polyfluorinated alcohols as fluoroalkylating reagents for a sequential one-pot transformation with ketones to R-CF-embedded 1,5-diketones and pyridines enabled by a nickel catalyst. The protocol is tolerant to a range of functional groups (>31 examples and up to 85% yield) and perfluoro alcohols and releases H and HO as byproducts. Preliminary mechanistic studies, EPR analyses, and deuterium scrambling experiments were performed, and observed / = 2.12.

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http://dx.doi.org/10.1021/acs.orglett.4c03478DOI Listing

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