Issue 3, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
02 Nov 2016
Accepted
11 Dec 2016
First published
13 Jan 2017

Org. Chem. Front., 2017,4, 335-342

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

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