Jump to main content
Jump to site search

Issue 3, 2017
Previous Article Next Article

Substrate-driven selective mono- and bis-couplings of ortho-(OTf/I/Br) substituted gem-dibromovinylarenes

Author affiliations

Abstract

A one-pot approach with the substrate-driven selective and competitive reactivity of ortho-trifloxy, iodo or bromo functionalized gem-dibromovinylarenes was studied under Pd-catalyzed conditions. These investigations provided synthetically important and structurally diverse functional ortho-alkynylbiaryls, ortho-alkynylbromoarenes, arene-1,2-diynes and diarylmethylidenefluorenes. The adopted protocol involving the in situ generation of 1-bromoalkyne from gem-dibromovinylarenes and their functionalization in pot- and atom-economical couplings employing triarylbismuths furnished a viable synthetic methodology with good to high yields. The present study also unveiled the substrate-driven selective mono- and bis-couplings using palladium catalyzed domino and sequential reaction protocols.

Graphical abstract: Substrate-driven selective mono- and bis-couplings of ortho-(OTf/I/Br) substituted gem-dibromovinylarenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Nov 2016, accepted on 11 Dec 2016 and first published on 13 Jan 2017


Article type: Research Article
DOI: 10.1039/C6QO00681G
Citation: Org. Chem. Front., 2017,4, 335-342
  •   Request permissions

    Substrate-driven selective mono- and bis-couplings of ortho-(OTf/I/Br) substituted gem-dibromovinylarenes

    M. L. N. Rao, P. Dasgupta and S. S. Islam, Org. Chem. Front., 2017, 4, 335
    DOI: 10.1039/C6QO00681G

Search articles by author

Spotlight

Advertisements