Copper-catalyzed asymmetric C(sp<sup>2</sup>)-H arylation for the synthesis of P- and axially chiral phosphorus compounds.

Yan, Shao-Bai; Wang, Rui; Li, Zha-Gen; Li, An-Na; Wang, Chuanyong; Duan, Wei-Liang · Nat Commun · 2023

basic_science · Level V

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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(sp<sup>2</sup>)-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.