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

Chemical Communications : Chem Comm
Yi-Long ZhuBo Jiang

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.

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Citations

Sep 1, 2018·Chemical Communications : Chem Comm·Min-Hua HuangBo Jiang
May 17, 2019·Organic Letters·Ji-Lin LiHonggen Wang

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