期刊
TETRAHEDRON
卷 73, 期 37, 页码 5509-5516出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.07.049
关键词
Sequential one-pot; C-H heteroarylation; Unsymmetrical scaffolds; Thiophene; Pyridine
We present C-H heteroarylation reactions between thiophene and variously substituted bromopyridines. The objective was to synthesize unsymmetrical 2,5-bipyridylthiophenes. We studied the reaction conditions allowing to a sequential one-pot double C-H heteroarylation, in a view to introduce two different pyridyl moieties at positions 2 and 5 of the thiophene ring using bromopyridines. 11 original unsymmetrical 2,5-bipyridylthiophenes were synthesized and characterized, including 2,5-di(pyridin-2yl)thiophenes for which the preparation by classical cross-coupling reactions is challenging. Finally, with the additional synthesis of both an unsymmetrical 2,5-biarylthiophene and an original pyrimidinthiophene-furan scaffold, we shown that our methodology was also an efficient tool to access to new heterocyclic sequences. (C) 2017 Elsevier Ltd. All rights reserved.
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