Rhodium(II)-Catalyzed Regioselective Remote C-H Alkylation of Protic Indoles

被引：28

作者：

Kong, Lingheng ^{[1
]}

Han, Xi ^{[1
]}

Chen, Haohua ^{[2
]}

Sun, Huaming ^{[1
]}

Lan, Yu ^{[1
]}

Li, Xingwei ^{[2
,3
]}

机构：

[1] Shaanxi Normal Univ SNNU, Sch Chem & Chem Engn, Xian 710062, Peoples R China

[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing 400030, Peoples R China

[3] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China

来源：

ACS CATALYSIS | 2021年 / 11卷 / 09期

基金：

中国博士后科学基金;

关键词：

rhodium; remote C-H functionalization; indole; diazo; alkylation; hydrogen bonding; DIRECTING GROUP; ARYLATION; ACTIVATION; FUNCTIONALIZATION; BORYLATION; ARENES; MILD; ALKENYLATION; ACCESS;

D O I：

10.1021/acscatal.1c01052

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Control of regioselectivity that defies the intrinsic reactivity of arene C-H bonds remains a formidable challenge. In this work, dimeric Rh(II) complexes have been applied as an efficient catalyst for the regioselective coupling of NH indoles with diazo compounds. Two-substituted indoles mostly reacted with C(6) selectivity. Mechanistic studies revealed that the regioselectivity results from the hydrogen-bonding directing effect, and the C-C bond formation proceeds via the Friedel-Crafts-type attack of indole toward the Rh(II) carbene species. In contrast, the reaction of 4-methoxyindoles occurred exclusively with the complementary C(7) selectivity.

引用

页码：4929 / 4935

页数：7

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