1,6-Nucleophilic Di- and Trifluoromethylation of -Quinone Methides with MeSiCFH/MeSiCF Facilitated by CsF/18-Crown-6.

Molecules

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Published: June 2024

The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of -quinone methides (-QMs) with MeSiRf (Rf = CFH, CF, CFCF, CFCOOEt, and CFSPh) under mild conditions are described. Although MeSiCFH shows lower reactivity than MeSiCF, it can react with -QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated -quinone methides and -fluoroalkylated diarylmethanes.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11206660PMC
http://dx.doi.org/10.3390/molecules29122905DOI Listing

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