Decarboxylative Acylation of Carboxylic Acids: Reaction Investigation and Mechanistic Study

被引:27
|
作者
Wu, Xiaopeng [1 ]
Han, Jie [1 ]
Xia, Siyu [1 ]
Li, Weipeng [1 ]
Zhu, Chengjian [1 ,2 ]
Xie, Jin [1 ,3 ]
机构
[1] Nanjing Univ, Chem & Biomed Innovat Ctr ChemB, Sch Chem & Chem Engn, State Key Lab Coordinat Chem,Jiangsu Key Lab Adv, Nanjing 210023, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Hunan Univ, Adv Catalyt Engn Res Ctr, Minist Educ, Changsha 410082, Hunan, Peoples R China
来源
CCS CHEMISTRY | 2022年 / 4卷 / 07期
基金
中国国家自然科学基金;
关键词
metallaphotoredox; decarboxylative acylation; ketones synthesis; dual-catalysis; carboxylic acid; FRIEDEL-CRAFTS ACYLATION; NICKEL CATALYSIS; PHOTOREDOX; ARYLATION;
D O I
10.31635/ccschem.021.202101197
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ketones serve as one of the most critical building blocks in organic synthesis, involving numerous functional group transformations. Herein, we rep ort an unprecedented photoredox-nickel metallap hotoredox-catalyzed decarboxylative acylation of common aliphatic acids with readily available aromatic and aliphatic thioesters. A wide range of structurally diverse asymmetrical aryl alkyl and dialkyl ketones have been constructed in yields of up to 98% with this strategy. The protocol has excellent reaction selectivity and functional group compatibility, representing a significant step forward in ketone synthesis. The one-pot decarboxylative acylation at the gram scale from two different carbox- synthesis of complex ketones shows its synthetic robustness. Both mechanistic experiments and density functional theory (DFT) calculations suggest that the decarboxylative acylation reaction operates via an underdeveloped Ni( I)-Ni(II)-Ni( I)Ni(III)-Ni(I) catalytic cycle. [GRAPHICS] .
引用
收藏
页码:2469 / 2480
页数:12
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