N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp2)–H bond

Pragati Biswal; Tanmayee Nanda; Shyam Kumar Banjare; Smruti Ranjan Mohanty; Ranjit Mishra; Ponneri C. Ravikumar

doi:10.1039/D2CC06048E

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N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp²)–H bond†

Pragati Biswal,‡^ab Tanmayee Nanda,‡^ab Shyam Kumar Banjare,^ab Smruti Ranjan Mohanty,^ab Ranjit Mishra

^ab and Ponneri C. Ravikumar

*^ab

Author affiliations

* Corresponding authors

^a School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatni, Odisha 752050, India
E-mail: pcr@niser.ac.in

^b Homi Bhabha National Institute (HBNI), Training School Complex, Anushaktinagar, Mumbai, India

Abstract

A Rh-catalyzed C(sp²)–H propenylation has been reported by taking N-allyl benzimidazole as an allylamine congener. This transformation has been observed for the first time, where a tandem process of C–H allylation followed by alkene isomerization delivers a highly stereoselective trans-propenylated product. Detailed mechanistic studies including the characterization of rhodacycle-intermediates have been conducted to understand the mechanism.

This article is part of the themed collection: 2023 Pioneering Investigators

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Article information

DOI: https://doi.org/10.1039/D2CC06048E
Article type: Communication
Submitted: 08 Nov 2022
Accepted: 30 Nov 2022
First published: 30 Nov 2022

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Chem. Commun., 2023,59, 199-202

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N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp²)–H bond

P. Biswal, T. Nanda, S. K. Banjare, S. R. Mohanty, R. Mishra and P. C. Ravikumar, Chem. Commun., 2023, 59, 199 DOI: 10.1039/D2CC06048E

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