Work

Copper‐Catalyzed Tandem Cyclization of 2‐(Alkynylaryl)Acetonitriles and Amines: Access to 3‐Hydroxyisoindolinones

Year: 2024

Type: article

Abstract: Herein, we describe an approach to the synthesis of 3‐hydroxyisoindolinone derivatives via copper‐catalyzed tandem cyclization of 2‐(alkynylaryl)acetonitriles and amines. This reaction is compatible with 2‐(alkynylaryl)acetonitriles and primary alkyl amines containing various functional groups, providing the corresponding 3‐hydroxyindolinone derivatives with yields ranging from 44%–82%. Preliminary mechanistic studies suggest that the reaction involves oxidation of the benzylic carbon, amide formation, hydration of the alkyne and intramolecular cyclization to produce various 3‐hydroxyisoindolinones. The practicality of the strategy was further demonstrated by gram‐scale synthesis, late‐stage functionalizations, and the post modification of natural products.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202400809

Authors: Jiatian Li, Lin Pan, Xiangwen Tan, Huanfeng Jiang, Wanqing Wu

Institutions: State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Basic and Applied Basic Research Foundation of Guangdong Province

Awards: G2099619119, G3754285485, G7839754299