Palladium-Catalyzed Domino Synthesis of 2,3-Difunctionalized Indoles via Migratory Insertion of Isocyanides in Batch and Continuous Flow

被引：14

作者：

Chen, Su ^{[1
]}

Oliva, Monica ^{[1
]}

Van Meervelt, Luc ^{[2
]}

Van der Eycken, Erik V. ^{[1
,3
]}

Sharma, Upendra K. ^{[1
]}

机构：

[1] Univ Leuven, Dept Chem, Lab Organ & Microwave Assisted Chem LOMAC, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[2] Katholieke Univ Leuven, Dept Chem, Biomol Architecture, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[3] Peoples Friendship Univ Russia, RUDN Univ, Miklukho Maklaya St 6, RU-117198 Moscow, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 13期

关键词：

Palladium-catalyzed cascade reaction; domino cyclizations; isocyanide insertion; triple bond activation; acyl indoles; MULTICOMPONENT REACTIONS; H FUNCTIONALIZATION; CONCISE SYNTHESIS; CYCLIZATION; CONSTRUCTION; TRYPROSTATIN; ISONITRILES; SPIROCYCLIZATION; CYCLOADDITION; HETEROCYCLES;

D O I：

10.1002/adsc.202100339

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report, herein, a palladium-catalyzed cascade comprising carbopalladation, migratory insertion of isocyanide and triple bond activation followed by a nucleophilic attack (OR-) to construct difunctionalized acyl indoles. The process involves multiple bond formations via key palladium-chemistry steps, to construct these bis-heterocycles containing two privileged scaffolds (indole and oxindole) in a single operational step, along with attempts to generate enantioselectivity at a quaternary carbon center. The methodology also demonstrates a continuous-flow process to synthesize aryl isocyanides within minutes and using them in a telescopic manner.

引用

页码：3220 / 3226

页数：7

共 90 条

[31] How to approach flow chemistry [J].