A General Access to Aryl-Alkyl Ketones via Nickel-Catalyzed Carbonylative Reductive Cross-Coupling Reactions

被引:0
|
作者
Su, Lei [1 ,2 ]
Gao, Shen [1 ,2 ]
Chen, Lijuan [2 ]
Yan, Jie [3 ]
Jiang, Yuanli [3 ,4 ]
Zheng, Qingshu [1 ,2 ]
Liu, Jiawang [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[3] Henan Energy Chem Grp Co Ltd, Zhengzhou 450046, Henan, Peoples R China
[4] Zhengzhou Univ, Sch Chem Engn, Zhengzhou 450001, Peoples R China
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
Aryl-alkyl ketones; Carbonylation; Nickel catalysis; Reductive cross-coupling; ASYMMETRIC HYDROFORMYLATION; ORGANOMETALLIC REAGENTS; HECK REACTION; DUAL NICKEL; ATM; AMIDES; ELECTROPHILES; ACYLATION; ALKENES; HALIDES;
D O I
10.1002/asia.202500214
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed carbonylation reactions have emerged as a versatile and powerful strategy for the production of diverse value-added carbonyl-containing compounds. Nevertheless, the carbonylative synthesis of alkyl ketones, particularly those incorporating secondary or tertiary alkyl fragments, remains underexplored and poses significant challenges. Herein, we present a nickel-catalyzed carbonylative reductive cross-coupling reaction to synthesize a wide range of aryl-alkyl ketones from readily available alkyl halides, aryl iodides, and Mo(CO)6. This protocol exhibits excellent compatibility with primary, secondary, and tertiary alkyl electrophiles as well as aryl electrophiles bearing electron-withdrawing or electron-donating groups, offering a general access to aryl-alkyl ketones under mild conditions. Mechanistic studies reveal that Mo(CO)6 not only serves as a safe and effective CO surrogate, but also plays a crucial role in facilitating the nickel carbonyl species, which is critical for promoting the selective synthesis of aryl-alkyl ketones.
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页数:9
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