康 · 学术 | Reaction of the Day No. 1505(康煕简介)

康 · 学术 | Reaction of the Day No. 1505(康煕简介)

(来源:康龙化成)

转自:康龙化成

General Method for Carbon-heteroatom Cross-coupling Reactions via Semiheterogeneous Red-light Metallaphotocatalysis

Geyang Song, Wei Zhang, Jiameng Song, Qi Li, Yuyu Feng, Hongyu Liang, Tengfei Kang, Jianyang Dong, Gang Li, Juan Fan, Xue-Peng Zhang,

Quan Gu, Chao Wang & Dong Xue*

Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, China.

—Nat.Commun., 2025, doi: org/10.1038/s41467-025-61812-z.

Recommended by Bingbing Chang_MC5

KEY WORDS: photo chemistry, Ni catalysis, cross-coupling (反应类型), C(sp3)–N, C(sp3)–N, C(sp3)–O, C(sp3)–S, C(sp3)–Se (成键类型), aryl halides, nucleophiles (反应物), carbon nitride, CN-OA-m, red-light (其他).

ABSTRACT: Combining transition-metal catalysis with photocatalysis has emerged as a valuable, complementary approach for achieving carbon-heteroatom crosscoupling 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. Prof. Dong Xue et al. 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 semiheterogeneous 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 photocatalyst is easily recovered and recycled, which makes it a promising new tool for the development of other reactions involving red-light metallaphotoredox catalysis.

C-N cross-coupling reactions of substrate scope

C-N/O cross-coupling

reactions

of

substrate

scope

C-O/S/Se cross-coupling reactions of substrate scope

Cross-coupling reactions of aryl chlorides

Cross-coupling reactions of bioactive molecules (selected)

Prof. Dong Xue et al. have developed a method for red-light-driven Nicatalyzed C-heteroatom cross-coupling reactions using CN-OA-mas a photocatalyst. The versatile Ni/red-light semiheterogeneous catalyst systemenables the formation of four different types of C-heteroatom bonds and has a broad substrate scope. Notably, the use of a low energy red light results in broad functional group tolerance, demonstrating the method’s excellent potential utility for pharmaceutical chemistry. Catalyst-recycling experiments demonstrated that the CNOA-m could be recovered and reused at least five times. This method provides a new platform for the development of other reactions involving red-light metallaphotoredox catalysis.

特别声明:[康 · 学术 | Reaction of the Day No. 1505(康煕简介)] 该文观点仅代表作者本人,今日霍州系信息发布平台,霍州网仅提供信息存储空间服务。

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