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A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines

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Abstract

A Pd(II)–Ag(I) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one-pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2-iodoanilines. Six new bonds (four C–C and two C–N) are formed in a one-pot fashion. A variety of diindolylmethanes were obtained in excellent yields (up to 94%) under mild reaction conditions and this strategy is amenable to gram scale synthesis also. The products were transformed into various synthetically useful compounds.

Graphical abstract: A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines

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Publication details

The article was received on 11 Jul 2017, accepted on 27 Jul 2017 and first published on 27 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01701D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines

    A. Kayet and V. K. Singh, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01701D

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