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

被引:9
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
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
收藏
页码:1475 / 1479
页数:5
相关论文
共 50 条
[41]   Cp*Co(III)-Catalyzed C-H Acylmethylation of Arenes by Employing Sulfoxonium Ylides as Carbene Precursors [J].
Ji, Shuying ;
Yan, Kelu ;
Li, Bin ;
Wang, Baiquan .
ORGANIC LETTERS, 2018, 20 (18) :5981-5984
[42]   Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage [J].
Prakash, Rashmi ;
Bora, Bidisha R. ;
Boruah, Romesh C. ;
Gogoi, Sanjib .
ORGANIC LETTERS, 2018, 20 (08) :2297-2300
[43]   Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions [J].
Kumar, Anil ;
Sherikar, Mahadev Sharanappa ;
Hanchate, Vinayak ;
Prabhu, Kandikere Ramaiah .
TETRAHEDRON, 2021, 101
[44]   Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation [J].
Jiang, Yuqin ;
Li, Pengfei ;
Zhao, Jie ;
Liu, Bingxian ;
Li, Xingwei .
ORGANIC LETTERS, 2020, 22 (19) :7475-7479
[45]   Rh(III)-Catalyzed C-H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles [J].
Liu, Chaoshui ;
Dai, Qiuzi ;
Li, Yaqian ;
Huang, Chuhan ;
Guo, Lijuan ;
Yang, Zi .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11) :7281-7289
[46]   Rh(III)-catalyzed C-H/C-C activation of benzoylacetonitriles and cyclization with CF3-imidoyl sulfoxonium ylides to 3-trifluoromethyl-isoquinolones [J].
Yang, Zuguang ;
Li, Pinyi ;
Chen, Zhengkai ;
Wu, Xiao-Feng .
JOURNAL OF CATALYSIS, 2023, 427
[47]   Rh(III)-Catalyzed C-H Activation/Annulation of N-Methyl Arylhydrazines with Iodonium Ylides toward Ring-fused Cinnolines [J].
Pan, Changduo ;
Yuan, Cheng ;
Chen, Dongdong ;
Chen, Yuefeng ;
Yu, Jin-Tao .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (02)
[48]   Rhodium-Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N-carbamoylindoles with Vinylene Carbonate [J].
Song, Jia-Lin ;
Xiao, Lin ;
Chen, Shao-Yong ;
Zheng, Yi-Chuan ;
Liu, Yan-Zhi ;
Zhang, Shang-Shi ;
Shu, Bing .
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) :1457-1464
[49]   Facile construction of hydrogenated azepino[3,2,1-hi]indoles by Rh(iii)-catalyzed C-H activation/[5+2] annulation of N-cyanoacetylindolines with sulfoxonium ylides [J].
Hu, Panjie ;
Zhang, Ying ;
Liu, Bingxian ;
Li, Xingwei .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (22) :3263-3266
[50]   Ru(II)- or Rh(III)-Catalyzed Annulation of Aromatic/Vinylic Acids withAlkylidenecyclopropanes via C-H Activation [J].
Ramesh, Balu ;
Jeganmohan, Masilamani .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) :5668-5681