Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light

Clarice A. D. Caiuby; Akbar Ali; Vinicius T. Santana; Francisco W. de S. Lucas; Marilia S. Santos; Arlene G. Corrêa; Otaciro R. Nascimento; Hao Jiang; Márcio W. Paixão

doi:10.1039/C8RA01787E

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Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light†

Clarice A. D. Caiuby,

^a Akbar Ali,^a Vinicius T. Santana,^b Francisco W. de S. Lucas,

^a Marilia S. Santos,^a Arlene G. Corrêa,

^a Otaciro R. Nascimento,

^b Hao Jiang^a and Márcio W. Paixão

*^a

Author affiliations

* Corresponding authors

^a Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos – UFSCar, Rodovia Washington Luís, km 235 – SP-310, São Carlos, São Paulo, Brazil 13565-905
E-mail: mwpaixao@ufscar.br

^b Group of Molecular Biophysics “Sérgio Mascarenhas”, São Carlos Institute of Physics – IFSC/USP, University of São Paulo, Avenida Trabalhador São Carlense, 400, São Carlos, SP, Brazil

Abstract

The combination of visible-light and tris(trimethylsilyl)silane promoting intramolecular reductive cyclization protocol for the synthesis of functionalized indolines and 2,3-dihydrobenzofurans has been developed. The transformations occur in the absence of transition metal and additional photocatalyst. In addition, quantum yield (Φ) was determined and electron paramagnetic resonance spectroscopy was performed to better understand the reaction pathway.

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Article information

DOI: https://doi.org/10.1039/C8RA01787E
Article type: Paper
Submitted: 28 Feb 2018
Accepted: 21 Mar 2018
First published: 05 Apr 2018
This article is Open Access

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RSC Adv., 2018,8, 12879-12886

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Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light

C. A. D. Caiuby, A. Ali, V. T. Santana, F. W. de S. Lucas, M. S. Santos, A. G. Corrêa, O. R. Nascimento, H. Jiang and M. W. Paixão, RSC Adv., 2018, 8, 12879 DOI: 10.1039/C8RA01787E

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Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light†

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Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light

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