![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://www.cambridge.org/engage/assets/public/coe/logo/orcid.png){kind=logo}
Abstract
Combining transition-metal catalysis with photocatalysis has emerged as a valuable, complementary approach for achieving carbon–heteroatom cross-coupling reactions. However, the need to use blue or high-energy near-UV light leads to problems with scalability, chemoselectivity, and catalyst deactivation, which have limited the synthetic applications of this combination. Herein, we report a method for red-light-driven nickel-catalyzed cross-coupling reactions of aryl halides with 11 different types of nucleophiles using a polymeric carbon nitride (CN-OA-m) as a photocatalyst. This semihomogeneous catalyst system enabled the formation of four different types of carbon–heteroatom bonds (C–N, C–O, C–S, and C–Se) with a wide range of substrates (more than 200 examples) with yields up to 94%. Moreover, the photocatalysts could be recovered and recycled, which makes it a promising new tool for the development of other reactions involving red-light metallaphotoredox catalysis.
Supplementary materials
Title
General Method for Carbon–Heteroatom Cross-Coupling Reactions via Semiheterogeneous Red-Light Metallaphotocatalysis
Description
Combining transition-metal catalysis with photocatalysis has emerged as a valuable, complementary approach for achieving carbon–heteroatom cross-coupling reactions. However, the need to use blue or high-energy near-UV light leads to problems with scalability, chemoselectivity, and catalyst deactivation, which have limited the synthetic applications of this combination. Herein, we report a method for red-light-driven nickel-catalyzed cross-coupling reactions of aryl halides with 11 different types of nucleophiles using a polymeric carbon nitride (CN-OA-m) as a photocatalyst. This semihomogeneous catalyst system enabled the formation of four different types of carbon–heteroatom bonds (C–N, C–O, C–S, and C–Se) with a wide range of substrates (more than 200 examples) with yields up to 94%. Moreover, the photocatalysts could be recovered and recycled, which makes it a promising new tool for the development of other reactions involving red-light metallaphotoredox catalysis.
Actions
