Intermolecular 1,4‐Difunctionalization of Conjugated Dienes Enabled by Palladium/Copper/Iodide Cooperation: Regioselective Construction of 3‐Pyrrolines
Year: 2025
Type: article
Abstract: 3‐Pyrrolines are important nitrogen‐containing five‐membered heterocycles. In recent years, significant progress has been made in developing synthetic methods for 3‐pyrrolines, including direct and efficient strategy for the 1,4‐difunctionalization of conjugated dienes. However, most existing approaches typically require pre‐activated nitrogen sources (nitrene precursor or imine) or rely on intramolecular reactions to enhance reactivity, enabling the construction of 3‐pyrrolines. The synthesis of 3‐pyrrolines via intermolecular reactions without using pre‐activated nitrogen sources remains a challenging task. In this study, we present an intermolecular 1,4‐difunctionalization of conjugated dienes for the synthesis of 3,4‐disubstituted 3‐pyrrolines, using a tosylamide (NH2Ts) as the nitrogen source. The reaction was facilitated through the cooperation of palladium(II), copper(I) and iodide. The resulting 3‐pyrrolines can be readily converted into various pyrroles and pyrrolidines through simple transformations.
Source: Advanced Synthesis & Catalysis
Authors: Jingjie Meng, Junwei Wang, Jingang Zhang, Zhengxing Wu, Zehua Yang, Wanbin Zhang
Institutions: Shanghai Jiao Tong University, University of South China
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Awards: G5509013603, G7196973924
OpenAlex ID: W4409250291