Issue 3, 2023

Divergent synthesis of bis(indolyl)methanes via FeIII-catalysed regioselective dehydrogenative coupling reactions: a biomimetic approach to 6,6′-bis-(debromo)-gelliusine F

Abstract

The divergent dehydrogenative coupling reactions of tryptamines with the catalysis of nontoxic FeIII salts in the presence of DDQ as the co-oxidant have been developed. Remarkably, the transformations feature a rapid and regioselective assembly of diverse 2,8′- and N1,8′-bis(indolyl) methane derivatives from readily-available starting materials by simply changing the FeIII salt and reaction temperature. Besides, the fast reaction rate, mild reaction conditions, low catalyst cost and easy operations make this methodology quite useful. The synthetic utility was further demonstrated in the biomimetic synthesis of 6,6′-bis-(debromo)-gelliusine F.

Graphical abstract: Divergent synthesis of bis(indolyl)methanes via FeIII-catalysed regioselective dehydrogenative coupling reactions: a biomimetic approach to 6,6′-bis-(debromo)-gelliusine F

Supplementary files

Article information

Article type
Paper
Submitted
08 Dec 2022
Accepted
15 Dec 2022
First published
15 Dec 2022

Org. Biomol. Chem., 2023,21, 639-643

Divergent synthesis of bis(indolyl)methanes via FeIII-catalysed regioselective dehydrogenative coupling reactions: a biomimetic approach to 6,6′-bis-(debromo)-gelliusine F

Y. Wu, M. Liu, Q. Wang, H. Tian, J. Fan, Y. Zhou, Y. Wang and X. Deng, Org. Biomol. Chem., 2023, 21, 639 DOI: 10.1039/D2OB02236B

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