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Issue 37, 2017
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Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon–sulfur bond activation: a new avenue to homocoupling reactions

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Abstract

The Pd-catalyzed, CN-directed unsymmetrical synthesis of 2,4′-bithiophenes via an unprecedented homocoupling reaction is described. The NH2/CN/SMe arrangement breaks the routine. The cooperative performance of the functional groups in thiophenes would open up a new vision in the field of metal catalysis homocoupling reactions by joining the electrophilic and nucleophilic motifs of the substrate. Furthermore, it is found that the α-chelating effect of the carbonyl group in amino thiophene offers a new class of synthetic protocols for C–N cross-coupling with arylboronic acids. The bidentate N,O-chelation provides a series of advantages such as copper-catalyzed, ligand- and base-free under open-flask conditions. Interestingly, the combination of the C–N cross-coupling/homocoupling reactions in a domino fashion led to the bithiophene adducts featuring the C(Ar)–N bond cleavage in the nitrogen that bridged between the two thiophene units.

Graphical abstract: Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon–sulfur bond activation: a new avenue to homocoupling reactions

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Publication details

The article was received on 02 Aug 2017, accepted on 29 Aug 2017 and first published on 07 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01923H
Citation: Org. Biomol. Chem., 2017,15, 7830-7840
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    Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon–sulfur bond activation: a new avenue to homocoupling reactions

    A. H. Vahabi, A. Alizadeh, H. R. Khavasi and A. Bazgir, Org. Biomol. Chem., 2017, 15, 7830
    DOI: 10.1039/C7OB01923H

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