Recyclable polymerized Lewis acid poly-BPh(C6F5)2 catalyzed selective N-formylation and N-methylation of amines with carbon dioxide and phenylsilanes

被引:6
作者
Zhai, Gaowen [1 ]
Liu, Qiang [1 ]
Ji, Jialan [1 ]
Wu, Youting [1 ]
Geng, Jiao [1 ]
Hu, Xingbang [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Peoples R China
基金
中国国家自然科学基金;
关键词
Carbon dioxide; N-formylation; N-methylation; Polymeric sterically-hindered borane; Amine; CO2 PROMOTED SYNTHESIS; REDUCTIVE FUNCTIONALIZATION; CONTAINING HETEROCYCLES; SECONDARY-AMINES; SILYL FORMATES; IONIC LIQUIDS; HYDROSILANES; HYDROGENATION; HYDROSILYLATION; TRANSFORMATION;
D O I
10.1016/j.jcou.2022.102052
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new boron-centered polymer, which is named poly-BPh(C6F5)(2) (polymerized-bis(perfluorophenyl)-(phenyl) borane) was designed and synthesized, which is found to be an efficient catalyst for selective N-formylation and N-methylation of amines using CO2 as C1 building block in the presence of hydrosilanes. Milder reaction conditions (even at room temperature and 1 bar of CO2), remarkable recyclability, tolerance against a variety of functional groups and excellent yields reveal the excellent stability and catalytic activity of poly-BPh(C6F5)(2). The process herein represents a simple, ecologically friendly and efficient route for CO2 chemical fixation into value-added chemicals.
引用
收藏
页数:10
相关论文
共 97 条
[1]   Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].
Addis, Daniele ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011
[2]   Recent progress in the catalytic transformation of carbon dioxide into biosourced organic carbonates [J].
Aomchad, Vatcharaporn ;
Cristofol, Alex ;
Della Monica, Francesco ;
Limburg, Bart ;
D'Elia, Valerio ;
Kleij, Arjan W. .
GREEN CHEMISTRY, 2021, 23 (03) :1077-1113
[3]   Separating Electrophilicity and Lewis Acidity: The Synthesis, Characterization, and Electrochemistry of the Electron Deficient Tris(aryl)boranes B(C6F5)3-n(C6Cl5)n (n=1-3) [J].
Ashley, Andrew E. ;
Herrington, Thomas J. ;
Wildgoose, Gregory G. ;
Zaher, Hasna ;
Thompson, Amber L. ;
Rees, Nicholas H. ;
Kraemer, Tobias ;
O'Hare, Dermot .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14727-14740
[4]   Non-Metal-Mediated Homogeneous Hydrogenation of CO2 to CH3OH [J].
Ashley, Andrew E. ;
Thompson, Amber L. ;
O'Hare, Dermot .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9839-9843
[5]   Phosphorus Lewis acids: emerging reactivity and applications in catalysis [J].
Bayne, J. M. ;
Stephan, D. W. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (04) :765-774
[6]   Aqua, alcohol, and acetonitrile adducts of tris(perfluorophenyl)borane: Evaluation of Bronsted acidity and ligand lability with experimental and computational methods [J].
Bergquist, C ;
Bridgewater, BM ;
Harlan, CJ ;
Norton, JR ;
Friesner, RA ;
Parkin, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10581-10590
[7]   Ruthenium-Catalyzed Direct Methylation of Primary and Secondary Aromatic Amines Using Carbon Dioxide and Molecular Hydrogen [J].
Beydoun, Kassem ;
vom Stein, Thorsten ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9554-9557
[8]   Catalytic Reductive N-Alkylations Using CO2 and Carboxylic Acid Derivatives: Recent Progress and Developments [J].
Cabrero-Antonino, Jose R. ;
Adam, Rosa ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (37) :12820-12838
[9]   Halogenated triarylboranes: synthesis, properties and applications in catalysis [J].
Carden, Jamie L. ;
Dasgupta, Ayan ;
Melen, Rebecca L. .
CHEMICAL SOCIETY REVIEWS, 2020, 49 (06) :1706-1725
[10]   Photochemical reduction of carbon dioxide to formic acid [J].
Cauwenbergh, Robin ;
Das, Shoubhik .
GREEN CHEMISTRY, 2021, 23 (07) :2553-2574