Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol

Xinxin Dang; Yu He; Yingtian Liu; Xuehong Chen; Jun-Long Li; Xian-Li Zhou; Hezhong Jiang; Jiahong Li

doi:10.1039/c8ra05443f

Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol

RSC Adv. 2018 Aug 24;8(52):30050-30054. doi: 10.1039/c8ra05443f. eCollection 2018 Aug 20.

Authors

Xinxin Dang¹, Yu He¹, Yingtian Liu¹, Xuehong Chen¹, Jun-Long Li², Xian-Li Zhou¹, Hezhong Jiang¹, Jiahong Li¹

Affiliations

¹ School of Life Science and Engineering, Southwest Jiaotong University Chengdu 610041 China jiahongljh@163.com jianghz10@home.swjtu.edu.cn zhouxl@swjtu.edu.cn.
² Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University Chengdu 610052 China.

Abstract

An efficient and convenient method to construct tetracyclic isoquinolinium salts via [Cp*RhCl₂]₂ catalyzed C-H activation and [4 + 2] annulation reactions in ethanol is described. This reaction is very fast and highly efficient in the green solvent ethanol. The reaction works with a broad substrate scope affording the products in good to excellent yields in a short time. Moreover, a ratio of S/C up to 10 000 could be achieved with gram scale synthesis.