Hydrogenations at Room Temperature and Atmospheric Pressure with Mesoionic Carbene-Stabilized Borenium Catalysts

被引：124

作者：

Eisenberger, Patrick ^{[1
]}

Bestvater, Brian P. ^{[1
]}

Keske, Eric C. ^{[1
]}

Crudden, Cathleen M. ^{[1
,2
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N5, Canada

[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

borenium; catalysis; hydrogenation; Lewis acids; mesoionic carbenes; N-HETEROCYCLIC CARBENE; FRUSTRATED LEWIS PAIRS; ASYMMETRIC HYDROGENATION; BORANE; ACIDITY; IMINES; ACTIVATION; REACTIVITY; CHEMISTRY; LIGANDS;

D O I：

10.1002/anie.201409250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,2,3-Triazolylidene-based mesoionic carbene boranes have been synthesized in a convenient one-pot protocol from the corresponding 1,2,3-triazolium salts, base, and borane. Borenium ions are obtained by hydride abstraction and serve as catalysts in mild hydrogenation reactions of imines and unsaturated N-heterocycles at ambient pressure and temperature.

引用

页码：2467 / 2471

页数：5

共 46 条

[1] Isolation of a C5-Deprotonated Imidazolium, a Crystalline "Abnormal" N-Heterocyclic Carbene [J].

Aldeco-Perez, Eugenia ;

Rosenthal, Amos J. ;

Donnadieu, Bruno ;

Parameswaran, Pattiyil ;

Frenking, Gernot ;

Bertrand, Guy .

SCIENCE, 2009, 326 (5952) :556-559

[2]

[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation

[3] Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation and Its Application in MIDA Boronate Synthesis [J].

Bagutski, Viktor ;

Del Grosso, Alessandro ;

Carrillo, Josue Ayuso ;

Cade, Ian A. ;

Helm, Matthew D. ;

Lawson, James R. ;

Singleton, Paul J. ;

Solomon, Sophia A. ;

Marcelli, Tommaso ;

Ingleson, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :474-487

[4] A convenient NMR method for the measurement of Lewis acidity at boron centres: Correlation of reaction rates of Lewis acid initiated epoxide polymerizations with Lewis acidity [J].

Beckett, MA ;

Strickland, GC ;

Holland, JR ;

Varma, KS .

POLYMER, 1996, 37 (20) :4629-4631

[5] Lewis acidity of tris(pentafluorophenyl) borane:: crystal and molecular structure of B(C6F5)3•OPEt3 [J].

Beckett, MA ;

Brassington, DS ;

Coles, SJ ;

Hursthouse, MB .

INORGANIC CHEMISTRY COMMUNICATIONS, 2000, 3 (10) :530-533

[6] syn-1,2-Carboboration of Alkynes with Borenium Cations [J].

Cade, Ian A. ;

Ingleson, Michael J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (40) :12874-12880

[7]

Chase P.A., 2007, Angewandte Chemie, V119, P8196, DOI DOI 10.1002/ANGE.200702908

[8] Lewis acid-catalyzed hydrogenation:: B(C6F5)3-mediated reduction of imines and nitriles with H2 [J].

Chase, Preston A. ;

Jurca, Titel ;

Stephan, Douglas W. .

CHEMICAL COMMUNICATIONS, 2008, (14) :1701-1703

[9] Metal-free catalytic hydrogenation [J].

Chase, Preston A. ;

Welch, Gregory C. ;

Jurca, Titel ;

Stephan, Douglas W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053

[10]

Chen D., 2010, Angewandte Chemie, V122, P9665, DOI 10.1002/ange.201004525

← 1 2 3 4 5 →