Ag-Catalyzed difluorohydration of β-alkynyl ketones for diastereoselective synthesis of 1, 5-dicarbonyl compounds. Issue 48 (15th May 2017)

• Record Type: Journal Article
• Authors: Zhu, Yi-Long; Wang, Ai-Fang; Du, Jian-Yu; Leng, Bo-Rong; Tu, Shu-Jiang; Wang, De-Cai; Wei, Ping; Hao, Wen-Juan; Jiang, Bo
• Is Part Of: Chemical communications. Volume 53:Issue 48(2017)
• Page Start: 6397
• Page End: 6400
• Publication Date: 2017-05-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc02088k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A new catalytic difluorohydration of β-alkynyl ketones using NFSI as the fluorinating reagent has been established, diastereoselectively providing difluoride 1, 5-dicarbonyl products, and some of them were converted into difluorinated isoquinolines. 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(sp 3 )–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(sp 3 )–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.