Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy

被引：11

作者：

Zhang, Bo-Sheng ^{[1
]}

Wang, Fan ^{[1
]}

Gou, Xue-Ya ^{[2
]}

Yang, Ying-Hui ^{[1
]}

Jia, Wan-Yuan ^{[1
]}

Liang, Yong-Min ^{[2
]}

Wang, Xi-Cun ^{[1
]}

Li, Yuke ^{[3
,4
]}

Quan, Zheng-Jun ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Int Sci & Technol Cooperat Base Water Reten, Lanzhou 730070, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong 999077, Peoples R China

[4] Chinese Univ Hong Kong, Ctr Sci Modeling & Computat, Shatin, Hong Kong 999077, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 19期

基金：

中国国家自然科学基金;

关键词：

REDUCTIVE ELIMINATION; ALKYLATION; ROUTE; FUNCTIONALIZATION; PALLADACYCLES;

D O I：

10.1021/acs.orglett.1c02715

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In palladium/norbornene (Pd/NBE) chemistry, the "ortho effect" has been proven to be a key factor in the process of beta-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the "ortho effect" and then undergo N-S bond cleavage with vinyl palladium, thus achieving a highly selective C-N coupling reaction in the Catallani-Lautens reaction system. On the basis of this discovery, a one-step synthesis of highly functionalized tricyclic indole derivatives was realized.

引用

页码：7518 / 7523

页数：6

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