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

被引：22
|
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
收藏
页码：4929 / 4935
页数：7
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