Work

Pd-catalyzed asymmetric P–C cross-coupling to access ortho-NH2 or -OH aryl P-chiral phosphine oxides

Year: 2025

Type: article

Abstract: A direct enantioselective P–C cross-coupling of secondary phosphine oxides with unprotected ortho -NH 2 or -OH aryl iodides is facilitated by a Pd-PHOX ligand catalyst. Here, we report a facile and straightforward approach for synthesizing free ortho -amino- or -hydroxy-substituted P-chiral phosphine oxides, achieving good yields and high ee values. Moreover, the chiral phosphine products derived from this process are successfully utilized to construct thiourea catalysts and potential bidentate Lewis base catalysts, which show promise in reductive aldol reactions. Additionally, density functional theory (DFT) calculations are performed to elucidate the origin of enantioselectivity and the generality of this method.

Source: Cell Reports Physical Science

DOI: 10.1016/j.xcrp.2025.102798

Authors: Haimeng Zhu, Kanon Takeda, Zhiping Yang, Ryo Takita, Jun (Joelle) Wang

Institutions: Hong Kong Baptist University, Shizuoka University, University of Shizuoka

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $5,620

Funders: Hong Kong Baptist University, National Natural Science Foundation of China, University Grants Committee, Japan Society for the Promotion of Science