通过铑（III）催化的C-H-烯丙基化/N-烷基化环化反应，由碳酸2-亚甲基三亚甲基酯温和合成3,4-二氢异喹啉-1(2)-酮
Mild Synthesis of 3,4-Dihydroisoquinolin-1(2)-ones via Rh(III)-Catalyzed Tandem C-H-Allylation/N-Alkylation Annulation with 2-Methylidenetrimethylene Carbonate.
作者信息
Xie Hui, Zeng Yao-Fu, Shu Bing, Liang Jin-Yi, Huang Zhuo-Jun, Chen Shao-Yong, Zheng Yi-Chuan, Liu Yan-Zhi, Zhang Shang-Shi
机构信息
Center for Drug Research and Development, Guangdong Pharmaceutical University, Guangzhou 510006, China.
Institute of Pharmacy and Pharmacology, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, University of South China, Hengyang 421000. China.
出版信息
J Org Chem. 2021 Dec 3;86(23):17063-17070. doi: 10.1021/acs.joc.1c02179. Epub 2021 Nov 19.
A tandem rhodium(III)-catalyzed system was established to access 3,4-dihydroisoquinolin-1(2)-one by coupling of -methoxy-3-methylbenzamide with 2-methylidenetrimethylene carbonate. This one-pot synthesis protocol processed smoothly under mild reaction conditions. Moreover, a total of 28 examples, broad substrate scope, and high functional-group compatibility were observed. Preliminary mechanism studies were also conducted and demonstrated that the rhodium(III) catalyst played a vital role in the C-H-allylation and N-alkylation cyclization process.
建立了一种串联铑（III）催化体系，通过将对甲氧基-3-甲基苯甲酰胺与2-亚甲基三亚甲基碳酸酯偶联来制备3,4-二氢异喹啉-1（2）-酮。该一锅法合成方案在温和的反应条件下顺利进行。此外，观察到总共28个实例、广泛的底物范围和高官能团兼容性。还进行了初步的机理研究，结果表明铑（III）催化剂在C-H-烯丙基化和N-烷基化环化过程中起着至关重要的作用。
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