C-H Functionalization Reactions of Unprotected N-Heterocycles by Gold-Catalyzed Carbene Transfer

被引：62

作者：

Jana, Sripati ^{[2
]}

Empel, Claire ^{[1
,2
]}

Pei, Chao ^{[2
]}

Aseeva, Polina ^{[2
]}

Nguyen, Thanh, V ^{[1
]}

Koenigs, Rene M. ^{[1
,2
]}

机构：

[1] Univ New South Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ACS CATALYSIS | 2020年 / 10卷 / 17期

关键词：

C-H functionalization; carbazole; carbene; gold; diazoalkanes; BOND FUNCTIONALIZATION; INSERTION; CARBAZOLE; DERIVATIVES; PHENOLS; LIGAND;

D O I：

10.1021/acscatal.0c02230

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：

The C-H functionalization reaction of N-heterocycles with an unprotected N-H group is one of the most step-economic strategies to introduce functional groups without the need for installation and removal of protecting groups. Despite recent significant advances in C-H functionalization chemistry, this strategy remains unsatisfactorily developed. In this report, we disclose a simple and straightforward protocol to allow for the selective C-H functionalization of unprotected double-benzannellated N-heterocycles via gold-catalyzed carbene-transfer reactions (29 examples, up to 86% yield). The scope of the reaction can also be expanded to the corresponding protected heterocycles (37 examples, up to 98% yield), further demonstrating the generality of this method. Mechanistic studies by density functional theory (DFT) calculations underpin the importance of the gold catalyst and reveal that the selectivity of this reaction is driven by trace amounts of water present in the reaction mixture.

引用

页码：9925 / 9931

页数：7