Citation: Dong Kui, Liu Qiang, Wu Li-Zhu. Cross-Coupling Hydrogen Evolution Reactions[J]. Acta Chimica Sinica, ;2020, 78(4): 299-310. doi: 10.6023/A19110412 shu

Cross-Coupling Hydrogen Evolution Reactions

Dong Kui ^a ,
Liu Qiang ^a,, ,
Wu Li-Zhu ^a,b,,

a.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
b.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Corresponding author: Liu Qiang, liuqiang@lzu.edu.cn Wu Li-Zhu, lzwu@mail.ipc.ac.cn
Received Date: 23 November 2019
Available Online: 11 March 2020
Fund Project: the Strategic Priority Research Program of the Chinese Academy of Sciences XDB17030200the National Natural Science Foundation of China 21390404Project supported by the National Natural Science Foundation of China (Nos. 21572090, 91427303, 21402217, 21390404), the Ministry of Science and Technology of China (Nos. 2013CB834804, 2013CB834505, 2014CB239402) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB17030200)the National Natural Science Foundation of China 21572090the Ministry of Science and Technology of China 2013CB834505the National Natural Science Foundation of China 21402217the Ministry of Science and Technology of China 2014CB239402the National Natural Science Foundation of China 91427303the Ministry of Science and Technology of China 2013CB834804

Figures(23)

During the past decade, transition metal-catalyzed dehydrogenative cross-couplings have emerged as an attractive strategy in synthetic chemistry due to its high step- and atom-economy as well as the less functionalized coupling partners. However, such reactions have to always use stoichiometric amount of sacrificial oxidants such as peroxides, high-valent metals (Cu salts, Ag salts, etc.), or iodine(Ⅲ) oxidants, thereby leading to possible generation of toxic wastes and making the process less desirable from a green chemistry perspective. The recently developed photocatalytic CCHE (cross-coupling hydrogen-evolution) reactions are a conceptually new type of reactions enabled by combination of photo-redox catalysis and proton reduction catalysis, wherein the photocatalyst uses light energy as the driving force for the cross-coupling and the hydrogen evolution catalyst may capture electrons and protons from the substrates or reaction intermediates to produce molecular hydrogen (H₂). Thus, without use of any sacrificial oxidant and under mild conditions, the dual catalyst system may afford cross-coupling products with excellent yields and an equivalent amount of H₂ as the sole byproduct. This kind of cross-coupling delivers a greener synthetic strategy and is particularly useful for reactions that involve species sensitive to traditional oxidants. In CCHE reactions, the raw materials are directly converted into products and hydrogen, the reactions are highly atom economy, environmentally friendly, and have attractive potential industrial application prospects. In this review, recent dramatic developments of photocatalytic and electrochemical CCHE reactions are discussed via the most prominent mechanistic pathways, the types of C-C bond, C-X (heteroatom) bond, or X-X bond formations and specific reaction classes.
- cross-coupling hydrogen evolution,
- visible-light photocatalysis,
- electrosynthesis,
- green chemistry,
- synthetic strategy
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沈阳化工大学材料科学与工程学院沈阳 110142