Jump to main content
Jump to site search

Issue 48, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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., 2017,53, 6397-6400
  •   Request permissions

    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, 53, 6397
    DOI: 10.1039/C7CC02088K

Search articles by author

Spotlight

Advertisements