Ag-Catalyzed difluorohydration of β-alkynyl ketones for diastereoselective synthesis of 1,5-dicarbonyl compounds

Yi Long Zhu, Ai Fang Wang, Jian Yu Du, Bo Rong Leng, Shu Jiang Tu, De Cai Wang, Ping Wei, Wen Juan Hao, Bo Jiang

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25 Scopus citations

Abstract

A new catalytic difluorohydration of β-alkynyl ketones using NFSI as the fluorinating reagent has been established, diastereoselectively furnishing a range of structurally diverse difluoride 1,5-dicarbonyl products through C(sp3)-H fluorination. Notably, the sterically encumbered t-butyl functionality located at the α-position of the carbonyl group of substrates 1 showed excellent diastereoselectivity (up to >99:1 dr). The reaction enabled multiple bond-forming events including two C(sp3)-F formation through Ag-catalysis to provide a highly efficient and practical method toward difluoride 1,5-dicarbonyls, some of which were successfully converted into difluorinated isoquinolines.

Original languageEnglish
Pages (from-to)6397-6400
Number of pages4
JournalChemical Communications
Volume53
Issue number48
DOIs
StatePublished - 2017

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