Synthesis of α, β and γ-carbolines via Pd-mediated Csp2-H/N–H activation

Shubhendu Dhara; Raju Singha; Atiur Ahmed; Haridas Mandal; Munmun Ghosh; Yasin Nuree; Jayanta K. Ray

doi:10.1039/C4RA08457H

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Synthesis of α, β and γ-carbolines via Pd-mediated C_sp²-H/N–H activation†

Shubhendu Dhara,^a Raju Singha,^a Atiur Ahmed,^a Haridas Mandal,^a Munmun Ghosh,^a Yasin Nuree^a and Jayanta K. Ray*^a

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* Corresponding authors

^a Department of Chemistry, Indian Institution of Technology Kharagpur, Kharagpur-721302, India
E-mail: jkray@chem.iitkgp.ernet.in
Fax: +91 3222282252
Tel: +91 3222283326

Abstract

An efficient method for the synthesis of halo-carbolines has been developed via Pd-catalysed formation of C–N bonds through C_sp²-H/N–H activation of 4-methyl-N-[2-(pyridine-3-yl)phenyl] benzenesulfonamide derivatives. Pd(OAc)₂ in the presence of Cu(OAc)₂ as oxidant afforded halo-carbolines in good to excellent yields with tolerance to a variety of substituents.

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Article information

DOI: https://doi.org/10.1039/C4RA08457H
Article type: Communication
Submitted: 10 Aug 2014
Accepted: 10 Sep 2014
First published: 10 Sep 2014

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RSC Adv., 2014,4, 45163-45167

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Synthesis of α, β and γ-carbolines via Pd-mediated C_sp²-H/N–H activation

S. Dhara, R. Singha, A. Ahmed, H. Mandal, M. Ghosh, Y. Nuree and J. K. Ray, RSC Adv., 2014, 4, 45163 DOI: 10.1039/C4RA08457H

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