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Combined experimental/theoretical study on D-glucosamine promoted regioselective sulfenylation of indoles catalyzed by copper

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Abstract

A combined experimental/theoretical investigation on the D-glucosamine promoted sulfenylation of indoles at the C3 position with sodium sulfinates catalyzed by copper is presented. The C3-sulfenylation of indoles shows good functional-group tolerance and yields. The 3-I-indole was identified as a crucial intermediate in the catalytic cycle. The catalytic role of [Cu(DMSO)2]2+ was addressed using quantum chemical calculations. In the interaction of [Cu(DMSO)2]2+ with indole, the [Cu(DMSO)2]2+ complex abstracts a hydrogen from the C3 of indole. The electronic origin for selective C–H bond activation of indole was revealed.

Graphical abstract: Combined experimental/theoretical study on d-glucosamine promoted regioselective sulfenylation of indoles catalyzed by copper

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Publication details

The article was received on 29 Jul 2017, accepted on 22 Sep 2017 and first published on 26 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02784B
Citation: New J. Chem., 2017, Advance Article
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    Combined experimental/theoretical study on D-glucosamine promoted regioselective sulfenylation of indoles catalyzed by copper

    X. Ge, F. Sun, X. Liu, X. Chen, C. Qian and S. Zhou, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02784B

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