Rh(II)/Pd(0) Dual Catalysis: Carbenoid N-H Insertion/Allylation Cascade Reaction to Construct Highly Functionalized and Polysubstituted Pyrrolidines

Maocheng Tang; Xianyan Jiao; Deping He; Ji-Xing Zhao; Ping Liu; Chun-Tian Li

doi:10.3390/molecules29245880

Rh(II)/Pd(0) Dual Catalysis: Carbenoid N-H Insertion/Allylation Cascade Reaction to Construct Highly Functionalized and Polysubstituted Pyrrolidines

Molecules. 2024 Dec 13;29(24):5880. doi: 10.3390/molecules29245880.

Authors

Maocheng Tang¹, Xianyan Jiao¹, Deping He¹, Ji-Xing Zhao², Ping Liu¹, Chun-Tian Li¹

Affiliations

¹ State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engneering, Shihezi University, Shihezi 832003, China.
² Analysis and Testing Center, Shihezi University, Shihezi 832003, China.

PMID: 39769971
DOI: 10.3390/molecules29245880

Abstract

In the category of drugs approved by the U.S. FDA, pyrrolidine is the most frequently used core of five-membered nonaromatic heterocycles containing nitrogen. Herein, a Rh(II)/Pd(0) dual-catalyzed carbenoid N-H insertion/allylation cascade reaction has been developed. This protocol provide an efficient approach for the construction of diverse highly functionalized and polysubstituted pyrrolidines in high yields (up to 91%) with excellent chemoselectivities and high diastereoselectivities (>20:1) under mild reaction conditions.

Keywords: Rh(II)/Pd(0) dual catalysis; allylation; carbenoid N-H insertion; high diastereoselectivities; pyrrolidines.

Grants and funding

RCZK2021B12; No. CXPY202205; No. KF202101/Shihezi University