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

Abstract

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

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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, Accepted Manuscript
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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, Accepted Manuscript , DOI: 10.1039/C8OB02118J

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