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Ligand‐Promoted Reactivity of Alkenes in Dehydrogenative Heck Reactions of Furans and Thiophenes
Author(s) -
Vasseur Alexandre,
Laugel Caroline,
Harakat Dominique,
Muzart Jacques,
Le Bras Jean
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403475
Subject(s) - chemistry , reactivity (psychology) , ligand (biochemistry) , stereoselectivity , heck reaction , alkene , catalysis , reaction mechanism , organic chemistry , medicinal chemistry , combinatorial chemistry , palladium , medicine , biochemistry , receptor , alternative medicine , pathology
4,5‐Diazafluorenone was found to promote the dehydrogenative Heck reaction of furans and thiophenes with hindered alkenes. High stereoselectivity was achieved in the synthesis of β,β‐diaryl α,β‐unsaturated alkenes. A mechanism, based on ESI‐MS studies, kinetic experiments, and competitive reactions, was proposed. The ligand influences C–H bond activation, insertion of the alkenes, the stereodetermining step, and the aerobic regeneration of the catalyst.