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

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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.

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

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Publication details

The article was received on 19 Mar 2017, accepted on 02 May 2017 and first published on 05 May 2017


Article type: Communication
DOI: 10.1039/C7CC02088K
Citation: Chem. Commun., 2017, Advance Article
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    Ag-Catalyzed difluorohydration of β-alkynyl ketones for diastereoselective synthesis of 1,5-dicarbonyl compounds

    Y. Zhu, A. Wang, J. Du, B. Leng, S. Tu, D. Wang, P. Wei, W. Hao and B. Jiang, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02088K

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