Silver-catalyzed Reductive Formylation of Amines with Carbon Dioxide

被引:2
作者
Uema, Seiya [1 ]
Sekine, Kenshiro [1 ]
Aoshima, Ryotaro [1 ]
Saito, Kodai [1 ]
Yamada, Tohru [1 ]
机构
[1] Keio Univ, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
基金
日本学术振兴会;
关键词
Carbon dioxide; Formylation; Silver catalyst; N-FORMYLATION; MOLECULAR-HYDROGEN; CO2; TRANSFORMATION; FUNCTIONALIZATION; PHENYLSILANE; ACTIVATION; FLUORIDE; SOLVENT;
D O I
10.1246/cl.230153
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The formylation of amines with carbon dioxide was examined in the presence of a catalytic amount of silver (II) picolinate and phenylsilane as a reductant. The reaction proceeded under base-free and mild conditions. The reaction conditions were successfully applied to both primary and secondary amines to afford the corresponding formamide derivatives in high yields. The formylation of amino acids, such as the proline and phenylalanine derivatives, proceeded by the present method to afford the corresponding formylated amine without racemization.
引用
收藏
页码:546 / 548
页数:3
相关论文
共 50 条
[21]   Silver-catalyzed Three-component Reaction of Propargylic Amines, Carbon Dioxide, and N-Iodosuccinimide for Stereoselective Preparation of (E)-Iodovinyloxazolidinones [J].
Sekine, Kohei ;
Kobayashi, Ryo ;
Yamada, Tohru .
CHEMISTRY LETTERS, 2015, 44 (10) :1407-1409
[22]   Silver-Catalyzed Carboxylation Reaction Using Carbon Dioxide as Carboxylative Reagent [J].
Zhang, Wen-Zhen .
CARBON DIOXIDE AND ORGANOMETALLICS, 2016, 53 :73-99
[23]   Silver-Catalyzed Efficient Synthesis of Vinylene Carbonate Derivatives from Carbon Dioxide [J].
Ugajin, Rie ;
Kikuchi, Satoshi ;
Yamada, Tohru .
SYNLETT, 2014, 25 (08) :1178-1180
[24]   A NHC-Silyliumylidene Cation for Catalytic N-Formylation of Amines Using Carbon Dioxide [J].
Leong, Bi-Xiang ;
Teo, Yeow-Chuan ;
Condamines, Cloe ;
Yang, Ming-Chung ;
Su, Ming-Der ;
So, Cheuk-Wai .
ACS CATALYSIS, 2020, 10 (24) :14824-14833
[25]   N-Formylation of Carbon Dioxide and Amines with EDTA as a Recyclable Catalyst under Ambient Conditions [J].
Zhou, Qiqi ;
Chen, Yu ;
Yuan, Xuexin ;
Yang, Hai-Jian ;
Jiang, Qingqing ;
Hu, Juncheng ;
Guo, Cun-Yue .
CATALYSTS, 2024, 14 (08)
[26]   A Titanium Dioxide Supported Gold Nanoparticle Catalyst for the Selective N-Formylation of Functionalized Amines with Carbon Dioxide and Hydrogen [J].
Mitsudome, Takato ;
Urayama, Teppei ;
Fujita, Shu ;
Maeno, Zen ;
Mizugaki, Tomoo ;
Jitsukawa, Koichiro ;
Kaneda, Kiyotomi .
CHEMCATCHEM, 2017, 9 (19) :3632-3636
[27]   Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide [J].
Moragas, Toni ;
Martin, Ruben .
SYNTHESIS-STUTTGART, 2016, 48 (17) :2816-2822
[28]   Cobalt-Catalyzed Reductive Carboxylation of Aryl Bromides with Carbon Dioxide [J].
Hang, Wei ;
Yi, Yaping ;
Xi, Chanjuan .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) :2337-2341
[29]   Reductive formylation of amines with CO2 using sodium borohydride: A catalyst-free route [J].
Hao, Leiduan ;
Zhang, Hongye ;
Luo, Xiaoying ;
Wu, Cailing ;
Zhao, Yanfei ;
Liu, Xinwei ;
Gao, Xiang ;
Chen, Yu ;
Liu, Zhimin .
JOURNAL OF CO2 UTILIZATION, 2017, 22 :208-211
[30]   DBU-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2 and Polymethylhydrosiloxane [J].
Li, Gang ;
Chen, Jie ;
Zhu, Dao-Yong ;
Chen, Ye ;
Xia, Ji-Bao .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) :2364-2369