Substrate-driven selective mono- and bis-couplings of ortho-(OTf/I/Br) substituted gem-dibromovinylarenes. Issue 3 (13th January 2017)

• Record Type: Journal Article
• Authors: Rao, Maddali L. N.; Dasgupta, Priyabrata; Islam, Sk Shamim
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 3(2017)
• Page Start: 335
• Page End: 342
• Publication Date: 2017-01-13
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00681g
• Languages: English
• ISSNs: 2052-4110

Abstract

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. 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.