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

Zheng Sun; Yu Shao; Shuwei Zhang; Yuxian Zhang; Yu Yuan; Xiaodong Jia

doi:10.1055/s-0040-1706010

Synthesis, Table of Contents

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

^aSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Yu Shao

^bSchool of Information Engineering, Yangzhou University, Huayang West Road 196, Yangzhou, Jiangsu 225127, P. R. of China

,

Shuwei Zhang

^aSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Yuxian Zhang

^aSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Yu Yuan∗

^aSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Xiaodong Jia∗

^aSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

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Abstract

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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

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References

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13 Analysis of the reaction solution of 1u by GC-MS showed that, besides the desired product, N-alkylisoindolin-1-one and N-alkyphthalimide as well as the C–N bond cleaved side-products were detected. We think that when intermediate B (Scheme 5) was generated, a series of competitive reactions, such as direct elimination to N-alkylisoindolin-1-one, over-oxidation of intermediate D to N-alkylphthalimide and hydrolysis of iminium intermediate F might occur, leading to decline of the yields of the desired product.
14 Benzoic acid together with a small amount of benzaldehyde were detected by GC-MS analysis.

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