PhI(OAc)2-mediated dearomative C–N coupling: facile construction of the spiro[indoline-3,2′-pyrrolidine] skeleton

Yali Zhou; Dengke Li; Shi Tang; Hongwei Sun; Jinbo Huang; Qiang Zhu

doi:10.1039/C8OB00343B

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PhI(OAc)₂-mediated dearomative C–N coupling: facile construction of the spiro[indoline-3,2′-pyrrolidine] skeleton†

Yali Zhou,^a Dengke Li,^a Shi Tang,^a Hongwei Sun,^a Jinbo Huang*^a and Qiang Zhu

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, China
E-mail: huang_jinbo@gibh.ac.cn, zhu_qiang@gibh.ac.cn
Fax: (+86) 20-3201-5299

Abstract

A facile construction of the spiro[indole-3,2′-pyrrolidine] skeleton, through diacetoxyiodobenzene (PIDA) mediated C–N bond-forming dearomatization of C3 sulfonamide linked indole derivatives, has been developed. A variety of spiro-indolepyrrolidines were obtained in moderate to excellent yields under mild conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB00343B
Article type: Communication
Submitted: 09 Feb 2018
Accepted: 01 Mar 2018
First published: 02 Mar 2018

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Org. Biomol. Chem., 2018,16, 2039-2042

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PhI(OAc)₂-mediated dearomative C–N coupling: facile construction of the spiro[indoline-3,2′-pyrrolidine] skeleton

Y. Zhou, D. Li, S. Tang, H. Sun, J. Huang and Q. Zhu, Org. Biomol. Chem., 2018, 16, 2039 DOI: 10.1039/C8OB00343B

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Organic & Biomolecular Chemistry