Ru(ii)-Catalyzed C-H bond activation/annulation of N-iminopyridinium ylides with sulfoxonium ylides

被引：10

作者：

Li, Xiang ^{[1
,2
]}

Li, Danlu ^{[1
]}

Zhang, Xiaofei ^{[1
,2
]}

机构：

[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Peoples R China

[2] Shaanxi Univ Sci & Technol, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 07期

基金：

中国国家自然科学基金;

关键词：

DIAZO-COMPOUNDS; ALKYNES; ISOCOUMARINS; ANNULATION; ALKENYLATION; CONSTRUCTION; BENZAMIDES; ARENES;

D O I：

10.1039/d1ob02427b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ru(ii)-catalyzed C-H bond activation/annulation of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method features broad substrate scope, high functional group tolerance, simple operation and silver salt-free conditions. Furthermore, the synthetic utility of this method is demonstrated by the alkenylation of the product and efficient synthesis of biologically active thunberginol A.

引用

页码：1475 / 1479

页数：5

共 50 条

[31] Rh(iii)-catalyzed C-H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones [J].

Duan, Yubo ;

Lu, Shu-Ning ;

Yang, Zuguang ;

Chen, Zhengkai ;

Wu, Xiao-Feng .

ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (15) :3843-3848

[32] Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes [J].

Xu, Youwei ;

Zhou, Xukai ;

Zheng, Guangfan ;

Li, Xingwei .

ORGANIC LETTERS, 2017, 19 (19) :5256-5259

[33] Rh(III)-catalyzed C-H acylmethylation of 2H-indazoles with sulfoxonium ylides [J].

Wang, Ya-Gai ;

Li, Jing ;

Wang, Xiao-Die ;

Shi, Linlin ;

Zhu, Xinju ;

Hao, Xin-Qi ;

Song, Mao-Ping .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2020, 24 (11) :850-856

[34] Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C-H Activation/Cyclopropanation Cascade [J].

Lou, Jiang ;

Wang, Quannan ;

Zhou, Yong-Gui ;

Yu, Zhengkun .

ORGANIC LETTERS, 2019, 21 (22) :9217-9222

[35] Synthesis of 1-naphthols via Cp*Co(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylides with alkynes [J].

Yu, Yongqi ;

Wu, Qianlong ;

Liu, Da ;

Yu, Lin ;

Tan, Ze ;

Zhu, Gangguo .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (23) :3868-3873

[36] α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C-H activation: a safe carbene precursor and a weak directing group [J].

Singh, Anurag ;

Kumar, Shreemoyee ;

Volla, Chandra M. R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (05) :879-909

[37] A Cascade Rh(III)-catalyzed C-H Activation/Chemodivergent Annulation of N-carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4-a]indol-1-ones Derivatives [J].

Xie, Hui ;

Zhong, Mei ;

Kang, Hua-Jie ;

Shu, Bing ;

Zhang, Shang-Shi .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) :1436-1442

[38] Maleimide-Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)-Catalyzed C-H Activation of Sulfoxonium Ylides [J].

Muthuraja, Perumal ;

Akhtar, Muhammad Saeed ;

Gopinath, Purushothaman ;

Lee, Yong Rok .

ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) :4595-4602

[39] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[40] Ru(II)-Catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes [J].

Baruah, Swagata ;

Kaishap, Partha Pratim ;

Gogoi, Sanjib .

CHEMICAL COMMUNICATIONS, 2016, 52 (88) :13004-13007

← 1 2 3 4 5 →