通过2-苯基吲哚的分子间/分子内顺序交叉脱氢偶联反应实现过渡金属控制合成11-苯并[]咔唑和6-亚烷基-6-异吲哚并[2,1-]吲哚
Transition-Metal-Controlled Synthesis of 11-Benzo[]carbazoles and 6-Alkylidene-6-isoindo[2,1-]indoles via Sequential Intermolecular/Intramolecular Cross-Dehydrogenative Coupling from 2-Phenylindoles.
作者信息
Liu Anyi, Han Qingshuai, Zhang Xiaofeng, Li Buhong, Huang Qiufeng
机构信息
Fujian Key Laboratory of Polymer Materials, College of Chemistry & Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, P.R. China.
MOE Key Laboratory of Optoelectronic Science and Technology for Medicine, Fujian Key Laboratory for Photonics Technology, Fujian Normal University, Fuzhou, Fujian 350007, P.R. China.
出版信息
Org Lett. 2019 Sep 6;21(17):6839-6843. doi: 10.1021/acs.orglett.9b02476. Epub 2019 Aug 13.
A catalyst-controlled synthesis of 11-benzo[]carbazoles and 6-alkylidene-6-isoindo[2,1-]indoles is described. Pd(OAc) favored 6-alkylidene-6-isoindo[2,1-]indoles via intramolecular C-H/N-H CDC reaction, while [Cp*RhCl] led to 11-benzo[]carbazoles through intramolecular C-H/C-H CDC reaction. Moreover, the synthesis of 11-benzo[]carbazoles via sequential intermolecular C-H/olefin coupling and intramolecular C3-H/olefin coupling from 2-phenylindoles and alkenes can be operated in one pot.
本文描述了一种由催化剂控制的11-苯并[]咔唑和6-亚烷基-6-异吲哚并[2,1-]吲哚的合成方法。醋酸钯（Pd(OAc)）通过分子内C-H/N-H交叉脱氢偶联反应（CDC反应）有利于生成6-亚烷基-6-异吲哚并[2,1-]吲哚，而[Cp*RhCl]则通过分子内C-H/C-H交叉脱氢偶联反应生成11-苯并[]咔唑。此外，由2-苯基吲哚和烯烃通过分子间C-H/烯烃偶联和分子内C3-H/烯烃偶联顺序合成11-苯并[]咔唑的反应可以在一个反应釜中进行。
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