Citation: Pengfei Zhang, Qingxue Ma, Zhiwei Jiang, Xiaohua Xu, Zhong Jin. Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template[J]. Chinese Chemical Letters, ;2024, 35(8): 109361. doi: 10.1016/j.cclet.2023.109361 shu

Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template

Pengfei Zhang ^a ,
Qingxue Ma ^a ,
Zhiwei Jiang ^a ,
Xiaohua Xu ^{a, *,} ,
Zhong Jin ^{a, b, *,}

a.
College of Chemistry, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
b.
Key Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry, College of Chemistry and Environmental Sciences, Kashi University, Kashgar 844007, China

xiaohuaxu@nankai.edu.cn

zjin@nankai.edu.cn

Received Date: 9 September 2023
Revised Date: 23 November 2023
Accepted Date: 3 December 2023
Available Online: 6 December 2023

Figures(6)

Transition-metal-catalyzed remote sp²C—H functionalization of aryl sulfonic acids was hardly ever realized owing to competitive ortho-C—H functionalization of aryl sulfonates and electron-deficient nature of phenyl ring. Herein, with the assistance of a practical biaryl indolyl directing template, palladium-catalyzed remote sp²C—H alkylation of aryl sulfonic acids have been achieved in moderate to good yields with exclusive meta selectivity. Moreover, remote meta-selective C—H alkynylation of aryl sulfonic acids was also accomplished with a rhodium catalyst. These meta-C—H functionalized products proved to be the superior synthetic precursors, which are difficult to access using the conventional strategy.
- C—H functionalization,
- Aryl sulfonic acid,
- Site-selectivity,
- Transition-metal catalysis,
- Alkylation,
- Alkynylation
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