Scalable Rhodaelectro-Catalyzed Expedient Access to Seven-Membered Azepino[3,2,1-hi]indoles via [5

被引：20

作者：

Yuan, Yumeng ^{[1
]}

Zhu, Jinlan ^{[1
]}

Yang, Zhongyuan ^{[2
,3
]}

Ni, Shao-Fei ^{[2
,3
]}

Huang, Qiufeng ^{[1
]}

Ackermann, Lutz ^{[4
]}

机构：

[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fujian Prov Key Lab Adv Mat Oriented Chem Engn, Fujian Key Lab Polymer Sci, Fuzhou 350007, Fujian, Peoples R China

[2] Shantou Univ, Dept Chem, Shantou 515063, Guangdong, Peoples R China

[3] Shantou Univ, Key Lab Preparat & Applicat Ordered Struct Mat Gu, Shantou 515063, Guangdong, Peoples R China

[4] Georg August Univ Gottingen, Wohler Res Inst Sustainable Chem, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

CCS CHEMISTRY | 2022年 / 4卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H activation; electrocatalysis; rhodium; annulation; indole; C-H ACTIVATION; ANNULATION; FUNCTIONALIZATION; BOND; ALKYLIDENECYCLOPROPANES; ELECTROCHEMISTRY; ALKYNYLATION; ALKYNES;

D O I：

10.31635/ccschem.022.202101654

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the establishment of a rhodaelectrocatalyzed [5 + 2] N-H/C-H oxidative annulation of alkynes by 7-arylindoles, enabling the synthesis of seven-membered azepino[3,2,1-hi]indoles using electricity as the sole oxidant. The reaction could be scaled up to gram-scale by flow-electrocatalysis. Two key rhodium(III) intermediates were isolated and fully characterized. Cyclovoltammetric analysis, X-ray photoelectron spectroscopy studies, and density functional theory calculations are suggestive of a rhodium(III-IV- II-III) manifold. [GRAPHICS]

引用

页码：1858 / 1870

页数：13

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