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Synthesis 2021; 53(09): 1663-1671
DOI: 10.1055/s-0040-1706010
paper

Oxidative Desymmetrization of Isoindolines Realized by tert-Butyl Nitrite (TBN) Initiated Radical sp3 C–H Activation Relay (CHAR)

Zheng Sun
a   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Yu Shao
b   School of Information Engineering, Yangzhou University, Huayang West Road 196, Yangzhou, Jiangsu 225127, P. R. of China
,
Shuwei Zhang
a   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Yuxian Zhang
a   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Yu Yuan∗
a   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Xiaodong Jia∗
a   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
› Author AffiliationsThis work was financially supported by National Natural Science Foundation of China (NNSFC, No. 21562038) for supporting our research. The authors also thank Natural Science Foundation of Jiangsu Province (BK20161328) for financial support.
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Abstract

An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp3 C–H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N-alkyl iso­indolines can be well tolerated. The mechanistic study shows that the C–H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.

Key words

radicals - C–H bond activation - oxidative desymmetrization - tert-butyl nitrite - isoindolines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706010.
  • Supporting Information


Publication History

Received: 26 November 2020

Accepted after revision: 14 December 2020

Article published online:
18 January 2021

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