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Issue 47, 2018
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Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols

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Abstract

An instant and efficient p-TSA·H2O-catalyzed sulfenylation reaction of 3-hydroxy bisindole derivatives is reported. This highly regioselective approach afforded C-3 functionalized products in excellent yield, and this methodology was found to be compatible with both aromatic and aliphatic thiols having electronic and steric divergence as well as diverse functional groups. The sulfenylation reaction was performed at room temperature with a green solvent with minimal catalyst loading and proceeded with the involvement of a quasi-antiaromatic-2H-indol-2-one ring intermediate. Moreover, the experimental results obtained for the sulfenylation reaction of 3-hydroxy bisindoles were supported by theoretical calculations in order to comprehend the regioselectivity and chemical reactivity observed in the thiolation reaction of 3-hydroxy bisindoles. The protocol involved the SN1 pathway, as also demonstrated by theoretical calculations.

Graphical abstract: Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols

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Publication details

The article was received on 29 Aug 2018, accepted on 31 Oct 2018 and first published on 05 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02118J
Citation: Org. Biomol. Chem., 2018,16, 9259-9268
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    Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols

    N. Sharma and R. K. Peddinti, Org. Biomol. Chem., 2018, 16, 9259
    DOI: 10.1039/C8OB02118J

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