ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Simple chiral sulfinyl imine–thioether ligands for Pd-catalyzed allylic alkylation

Ge-Yun You, Xiao-Feng Liu, Pei-Wen Fang, Lu-Fang Liang, Cheng-Hao Dai, and Bin Feng

Key Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, Baise, China

E-mail: fengbinjy@163.com

Received: 11 December 2021  Accepted: 5 March 2022

Abstract:

A set of chiral sulfinyl imine–thioether ligands are prepared via dehydration condensation of substituted benzaldehyde and chiral sulfinamide. The activity of these ligands in Pd-catalyzed asymmetric allylic alkylation reaction is studied, and the results indicate that the structure of sulfinamide motifs has an obvious effect on the e.r. value and yield. The chiral p-tolylsulfinamide derived ligands can promote the reaction efficiently, while the ligands with tert-butyl group fail to catalyze the reaction. Then, the substrate scope is also investigated under the optimal reaction conditions.

Keywords: Chiral ligand; Thioether; Sulfinyl imine; Asymmetric catalysis; Allylic alkylation reaction

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02176-2

Chemical Papers 76 (7) 4615–4620 (2022)