Synthesis of π-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions

TETRAHEDRON

卷:72

Article

Castro, M. Cidalia R.¹  Raposo, M. Manuela M.¹ 

[1] Univ Minho, Ctr Chem, Campus Gualtar, P-4710057 Braga, Portugal

关键词: pi-Conjugated systems;    Formyl-substituted (bi)thienylpyrroles;    Thiophene;    Pyrrole;    Suzuki-Miyaura coupling;    Stifle coupling;    Decarboxylative coupling;    UV-vis spectroscopy;    Nonlinear optical (NLO) precursors;   

DOI  :  10.1016/j.tet.2016.02.054

来源: Elsevier

【 摘 要 】

A series of thienylpyrroles and bithienylpyrroles together with their formyl derivatives 5a-d were synthesized using commercially or readily available coupling components, through three different palladium catalyzed cross-coupling reactions (Suzuki-Miyaura, Stille and decarboxylative coupling). The synthesis of compounds 5 via the Suzuki-Miyaura reaction produced the title compounds in better yields than the other coupling reactions, while, decarboxylative coupling resulted in the lower yields. UV-visible and H-1 NMR studies confirm the existence of significant intramolecular charge transfer (ICT) from the donor pyrrole heterocycle to the acceptor group and a high polarizability of the whole pi-conjugated systems. Together these characteristics indicate their strong potential as versatile precursors for the preparation of push-pull heterocyclic compounds for optical applications. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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