Copper-catalyzed asymmetric C(sp2)-H arylation for the synthesis of P- and axially chiral phosphorus compounds

Shao-Bai Yan; Rui Wang; Zha-Gen Li; An-Na Li; Chuanyong Wang; Wei-Liang Duan

doi:10.1038/s41467-023-37987-8

Copper-catalyzed asymmetric C(sp²)-H arylation for the synthesis of P- and axially chiral phosphorus compounds

Nat Commun. 2023 Apr 20;14(1):2264. doi: 10.1038/s41467-023-37987-8.

Authors

Shao-Bai Yan¹, Rui Wang¹, Zha-Gen Li¹, An-Na Li¹, Chuanyong Wang¹, Wei-Liang Duan^{2

3

4}

Affiliations

¹ College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, 225002, Yangzhou, China.
² College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, 225002, Yangzhou, China. duanwl@yzu.edu.cn.
³ College of Chemistry and Chemical Engineering, Inner Mongolia University, 235 West University Street, 010021, Hohhot, China. duanwl@yzu.edu.cn.
⁴ School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, 710119, Xi'an, China. duanwl@yzu.edu.cn.

Abstract

Transition metal-catalyzed C-H bond functionalization is an important method in organic synthesis, but the development of methods that are lower cost and have a less environmental impact is desirable. Here, a Cu-catalyzed asymmetric C(sp²)-H arylation is reported. With diaryliodonium salts as arylating reagents, a range of ortho-arylated P-chiral phosphonic diamides were obtained in moderate to excellent yields with high enantioselectivities (up to 92% ee). Meanwhile, enantioselective C-3 arylation of diarylphosphine oxide indoles was also realized under similar conditions to construct axial chirality.

Abstract

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