Highly efficient low-valence tungsten-catalyzed deoxygenative reduction of tertiary amides to amines with pinacolborane

被引：0

作者：

Cheng, Biao ^{[1
]}

Xv, Jialong ^{[1
]}

Ren, Xiang ^{[2
]}

Li, Yuanyuan ^{[1
]}

Ji, Xiaoming ^{[1
]}

Lu, Zhan ^{[2
]}

机构：

[1] Henan Agr Univ, Coll Tobacco Sci, Flavors & Fragrance Engn & Technol Res Ctr Henan P, Zhengzhou 450046, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310058, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2025年

基金：

中国国家自然科学基金;

关键词：

HYDROBORATION REDUCTION; DECATUNGSTATE ANION; SECONDARY AMIDES; HYDROGENATION; COMPLEXES; PHOTOCHEMISTRY; SELECTIVITY; MOLYBDENUM; CHEMISTRY; CARBON;

D O I：

10.1039/d4qo02340d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient low-valence tungsten-catalyzed deoxygenative reduction of tertiary amides to amines with pinacolborane (HBPin) is developed. This protocol uses commercially available W(CO)6 as a catalyst in a solution of hexane under the irradiation of visible light without other additives, and the TON is up to 2000.

引用

页数：7

共 42 条

[21] Highly Selective, Efficient Deoxygenative Hydrogenation of Amides Catalyzed by a Manganese Pincer Complex via Metal-Ligand Cooperation
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[23] Conformal surface intensive doping of low-valence Bi on Cu2O for highly efficient electrochemical nitrate reduction to ammonia production
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[24] Hydrosilylative Reduction of Tertiary Amides to Amines Catalyzed by N-(Phosphinoaryl)anilido Complexes of Iron and Cobalt
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[25] Highly atom efficient guanylation of both aromatic and secondary amines catalyzed by simple lanthanide amides
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[26] Highly Active, Low-Valence Molybdenum- and Tungsten-Amide Catalysts for Bifunctional Imine-Hydrogenation Reactions
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[27] A SIMPLE AND HIGHLY EFFICIENT SYNTHESIS OF QUINOLINE TERTIARY AMINES CATALYZED BY HUNIG'S BASE
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