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Transition‐Metal‐Free Approach for the Direct Arylation of Thiophene: Experimental and Theoretical Investigations towards the (Het)‐Aryne Route
Author(s) -
Demangeat Catherine,
Saied Tarak,
Ramozzi Romain,
Ingrosso Francesca,
RuizLopez Manuel,
Panossian Armen,
Leroux Frédéric R.,
Fort Yves,
Comoy Corinne
Publication year - 2019
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.201801173
Subject(s) - aryne , thiophene , aryl , chemistry , ligand (biochemistry) , combinatorial chemistry , coupling reaction , density functional theory , transition metal , computational chemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , alkyl , receptor
This paper presents the results of our investigations on the arylation of thiophene using the transition‐metal‐free “aryne coupling” methodology. The reaction was studied by both experiment and computation (density functional theory) and comparison with phenyllithium was established. In parallel, the effects of the ligand and the salt on the coupling reaction were examined. The results underline the remarkable effect of such additives on the coupling reaction and the potency of the method to construct hetaryl–aryl backbones which open up promising access to a wide range of heterobiaryl structures using the novel “Het‐Aryne” route.