Photoredox/nickel dual catalyzed stereospecific synthesis of distal alkenyl ketones

The selective C-C bond deconstruction/refunctionalization via a photoredox/nickel dual-catalyzed hydroalkylation of alkynes is developed under mild reaction conditions. In this protocol, a broad range of alkyl- and aryl-alkynes could react smoothly with cycloalkanols, affording the corresponding distal and site-specific vinyl-substituted ketones with high yields and excellent regioselectivities. Moreover, DFT calculations verified that the electron-rich behavior of aromatics and weak Bronsted bases have a common effect on the photocatalytic oxidant ring-opening of cyclobutanols.

Automated summary

A selective C-C bond deconstruction/refunctionalization method via a photoredox/nickel dual catalysis has been developed, allowing a broad range of alkyl- and aryl-alkynes to react smoothly with cycloalkanols to yield distal, site-specific vinyl-substituted ketones with high yields and excellent regioselectivities. DFT calculations confirmed the electron-rich behavior of aromatics and weak Bronsted bases have a common effect on the photocatalytic oxidant ring-opening of cyclobutanols.