Photocatalytic C(sp2)-C(sp3) Cross-coupling between C(sp2)-Cl Bond and C(sp3)-H Bond

doi:10.6023/cjoc202605031

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光催化C(sp²)-Cl键与C(sp³)-H键的C(sp²)-C(sp³)交叉偶联

何晓君^a,b, 陈彬^a,b, 郭晓宁^a,b, 佟振合^a,b, 吴骊珠^*,a,b

^a中国科学院理化技术研究所光化学转换与功能材料重点实验室中国科学院-香港大学新材料合成和检测联合实验室新基石科学实验室北京 100190;
^b中国科学院大学未来技术学院北京 100049

收稿日期:2026-05-31 修回日期:2026-06-25
基金资助:
国家重点研发计划(No. 2022YFA1503200, 2021YFA1500100)、国家自然科学基金(No. 22588101, 22193013和22571310)、中国科学院战略性先导科技专项(No. XDB0960000)、中国科学院基础研究领域青年科学家项目(No. Grant No. YSBR-142)和新基石科学基金会资助项目.

Photocatalytic C(sp²)-C(sp³) Cross-coupling between C(sp²)-Cl Bond and C(sp³)-H Bond

Xiao-Jun He^a,b, Bin Chen^a,b, Xiao-Ning Guo^a,b, Chen-Ho Tung^a,b, Li-zhu Wu^a,b,*

^aKey Laboratory of Supramolecular Photochemistry and HKU-CAS Joint Laboratory on New Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China;
^bSchool of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049, P. R. China

Received:2026-05-31 Revised:2026-06-25
Contact: ^*E-mail: lzwu@mail.ipc.ac.cn
Supported by:
National Key R&D Program of China (No. 2022YFA1503200, 2021YFA1500100), the National Natural Science Foundation of China (No. 22588101, 22193013 and 22571310), the Strategic Priority Research Program of the Chinese Academy of Science (No. XDB0960000), the CAS Project for Young Scientists in Basic Research (No. Grant No. YSBR-142) and New Cornerstone Science Foundation.

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Abstract

Cross-coupling between C(sp²)-Cl bond and C(sp³)-H bond is an essential way to construct C(sp²)-C(sp³) bond. By merging photosensitizer and nickel catalyst, photocatalytic system proceeds the reactions under mild and efficient condition, which enriches the activation fashion of C(sp³)-H bond. It is commonly accepted that the reaction undergoes the catalytic cycle containing Ni(0) species. Herein, we report that when carbazole is utilized as a photosensitizer, Ni(I) rather than Ni(0) species is the primary nickel species in the system. The cooperation between carbazole photosensitizer and Ni(I) species exhibits competent catalytic ability to the cross-coupling of C(sp²)-Cl bond in aryl chloride and C(sp³)-H bond in good to excellent yields.

Key words: C(sp²)-C(sp³) cross-coupling, nickel species at low valance state, photocatalysis

Cite this article

Xiao-Jun He, Bin Chen, Xiao-Ning Guo, Chen-Ho Tung, Li-zhu Wu. Photocatalytic C(sp²)-C(sp³) Cross-coupling between C(sp²)-Cl Bond and C(sp³)-H Bond[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202605031.

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光催化C(sp²)-Cl键与C(sp³)-H键的C(sp²)-C(sp³)交叉偶联

Photocatalytic C(sp²)-C(sp³) Cross-coupling between C(sp²)-Cl Bond and C(sp³)-H Bond

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光催化C(sp2)-Cl键与C(sp3)-H键的C(sp2)-C(sp3)交叉偶联