Design and synthesis of a new family of planar and central chiral ferrocenyl phosphine ligands

Li Ling; Zeli Song; He Shan; Chao Wang; Shouting Li; Yanjiao Wang; Jianfeng Hu; Qian Chen; Hao Zhang; Yong Yang

doi:10.1039/d2cc06492h

Design and synthesis of a new family of planar and central chiral ferrocenyl phosphine ligands

Chem Commun (Camb). 2023 Mar 2;59(19):2739-2742. doi: 10.1039/d2cc06492h.

Authors

Li Ling^{1

2}, Zeli Song^{1

2}, He Shan^{1

2}, Chao Wang^{1

2}, Shouting Li^{1

2}, Yanjiao Wang^{1

2}, Jianfeng Hu^{1

2}, Qian Chen³, Hao Zhang^{1

2}, Yong Yang^{4

5}

Affiliations

¹ College of Chemistry & Chemical Engineering, Inner Mongolia University, Hohhot 010021, P. R. China. haozhang@imu.edu.cn.
² Inner Mongolia Key Laboratory of Fine Organic Synthesis, Inner Mongolia University, Hohhot 010021, P. R. China.
³ College of Chemical Engineering, Southwest Forestry University, Kunming, 650224, P. R. China.
⁴ State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, Shanxi 030001, P. R. China. yyong@sxicc.ac.cn.
⁵ National Energy Center for Coal to Clean Fuels, Synfuels China Co., Ltd., Huairou District, Beijing 101400, P. R. China.

PMID: 36744593
DOI: 10.1039/d2cc06492h

Abstract

A family of planar chiral indene-fused ferrocenes were prepared through an intramolecular asymmetric C-H arylation in excellent yields (up to 99%) with excellent enantioselectivities (up to 99% ee). They were thereafter successfully transformed to chiral ferrocenyl phosphines, featuring both planar and central chiralities, in good yields (up to 83%) and excellent diastereoselectivities (up to 99% de) through highly diastereoselective phosphination. This protocol offers a general method for planar and central chiral ferrocenyl phosphines. The potential applications of the newly developed ligands were demonstrated by a Pd-catalyzed enantioselective allylic alkylation reaction, in which high enantioselectivity (92% ee) and good yield (89%) were obtained.