Issue 33, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Jul 2017
Accepted
27 Jul 2017
First published
27 Jul 2017

Org. Biomol. Chem., 2017,15, 6997-7007

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, 15, 6997 DOI: 10.1039/C7OB01701D

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