4.5 Article

Copper-Promoted Thiolation of C(sp2)-H Bonds Using a 2-Amino Alkylbenzimidazole Directing Group

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 16, Pages 2280-2289

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700147

Keywords

Nitrogen heterocycles; Copper; C-H activation; Directing groups; Sulfur

Funding

  1. National Natural Science Foundation of China [21272217, 21472176]

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A copper-promoted thiolation of C(sp(2))-H bonds with disulfides was achieved by using 2-amino alkylbenzimidazole (MBIP amine) as a new and removable N,N-bidentate directing group. This strategy gives a variety of functionalized thioethers in moderate to excellent yields in a simple and efficient way. Importantly, the substrate scope is not limited to aromatic amides; diverse alkenyl amides are also compatible. Furthermore, this synthetic approach provides a potentially feasible way to achieve structural modification of related benzimidazole-containing compounds through direct C-H activation.

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