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

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(2))-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. Although transition metal-catalyzed C-H bond functionalization is a widely used method in organic synthesis, many methods rely on metals of low abundance. Here, the authors report a copper-catalyzed, asymmetric C-H arylation using diaryliodonium salts.

Automated summary

This paper reports a Cu-catalyzed asymmetric C(sp(2))-H arylation using diaryliodonium salts, which enables the synthesis of a range of chiral phosphonic diamides and chiral phosphine oxide indoles with high selectivity under mild conditions.