Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp2–H functionalization

Pratik A. Ambasana; Dipak D. Vachhani; Marzia Galli; Jeroen Jacobs; Luc Van Meervelt; Anamik K. Shah; Erik V. Van der Eycken

doi:10.1039/C4OB01644K

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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via C_sp²–H functionalization†

Pratik A. Ambasana,^ab Dipak D. Vachhani,*^a Marzia Galli,‡^a Jeroen Jacobs,^c Luc Van Meervelt,^c Anamik K. Shah^b and Erik V. Van der Eycken*^a

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* Corresponding authors

^a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, Belgium
E-mail: erik.vandereycken@chem.kuleuven.be, ddvachhani@gmail.com

^b Department of Chemistry, Saurashtra University, Rajkot – 360005, India

^c Biomolecular Architecture, Department of Chemistry, University of Leuven (KULeuven), Celestijnenlaan 200F, Leuven, Belgium

Abstract

The tuning of selective ring closure is a nontrivial challenge in synthetic organic chemistry. Herein we report a solvent switchable metal-free [4 + 2] cycloaddition approach via C_sp²–H functionalization. The protocol is highly atom economical with water being the only by-product, delivering N-substituted benzo[e]- or [f]isoindolones in high yields.

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Article information

DOI: https://doi.org/10.1039/C4OB01644K
Article type: Paper
Submitted: 01 Aug 2014
Accepted: 17 Sep 2014
First published: 18 Sep 2014
This article is Open Access

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Org. Biomol. Chem., 2014,12, 8861-8865

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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via C_sp²–H functionalization

P. A. Ambasana, D. D. Vachhani, M. Galli, J. Jacobs, L. Van Meervelt, A. K. Shah and E. V. Van der Eycken, Org. Biomol. Chem., 2014, 12, 8861 DOI: 10.1039/C4OB01644K

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Organic & Biomolecular Chemistry