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Dissymmetrization of Benzothiadiazole by Direct C–H Arylation: A Way to Symmetrical and Unsymmetrical Elongated π‐Conjugated Molecules
Author(s) -
Dall'Agnese Chunxiang,
Hernández Maldonado Daniel,
Le Borgne Damien,
MoineauChane Ching Kathleen I.
Publication year - 2017
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.201701382
Subject(s) - chemistry , conjugated system , palladium , molecule , environmentally friendly , selectivity , combinatorial chemistry , phosphine , block (permutation group theory) , acceptor , organic chemistry , catalysis , polymer , ecology , geometry , mathematics , physics , biology , condensed matter physics
5‐(7‐Bromo‐2,1,3‐benzothiadiazol‐4‐yl)‐2‐thiophenecarbaldehyde is a small building block of great interest for its use in the elaboration of symmetrical or unsymmetrical donor–acceptor π‐conjugated molecules for optoelectronic applications. Herein, a convenient, one‐pot, two‐component synthesis of this intermediate is reported, based upon a palladium‐catalysed, phosphine‐ and additive‐free, direct C–H arylation process. The synthesis has been studied in depth to obtain optimum yields and selectivity by an efficient and environmentally friendly strategy for sustainable synthesis.