1-Butyl-3-methylimidazol-2-ylidene Borane: A Readily Available, Liquid N-Heterocyclic Carbene Borane Reagent

被引：16

作者：

Bolt, Daniel K. ^{[1
]}

Curran, Dennis P. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 24期

基金：

美国国家科学基金会;

关键词：

NHC-BORANES; REDUCTIONS; ALDEHYDES; KETONES;

D O I：

10.1021/acs.joc.7b02730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Butyl-3-methylimidazol-2-ylidene borane has been synthesized directly from two inexpensive commercial reagents: 1-butyl-3-methylimidazolium bromide and sodium borohydride. This NHC-borane reagent is a stable, free-flowing liquid that shows promise for use in radical, ionic, and metal-catalyzed reactions.

引用

页码：13746 / 13750

页数：5

共 26 条

[1] Monoborane NHC Adducts in the Coordination Sphere of Transition Metals [J].

Bissinger, Philipp ;

Braunschweig, Holger ;

Kupfer, Thomas ;

Radacki, Krzysztof .

ORGANOMETALLICS, 2010, 29 (17) :3987-3990

[2] Synthesis and Reactions of N-Heterocyclic Carbene Boranes [J].

Curran, Dennis P. ;

Solovyev, Andrey ;

Brahmi, Malika Makhlouf ;

Fensterbank, Louis ;

Malacria, Max ;

Lacote, Emmanuel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) :10294-10317

[3]

Dake S.A., 2014, GREEN CHEM SYNTHESIS, P201, DOI 10.1007/978-81-322-1850-0_7

[4] 1,3-Dimethylimidazoyl-2-ylidene borane [J].

Gardner, Sean ;

Kawamoto, Takuji ;

Curran, Dennis P. .

ORGANIC SYNTHESES, 2015, 92 :342-+

[5] Synthesis of 1,3-Dialkylimidazol-2-ylidene Boranes from 1,3-Dialkylimidazolium Iodides and Sodium Borohydride [J].

Gardner, Sean ;

Kawamoto, Takuji ;

Curran, Dennis P. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) :9794-9797

[6] N-Heterocyclic Carbene Boranes are Good Hydride Donors [J].

Horn, Markus ;

Mayr, Herbert ;

Lacote, Emmanuel ;

Merling, Everett ;

Deaner, Jordan ;

Wells, Sarah ;

McFadden, Timothy ;

Curran, Dennis P. .

ORGANIC LETTERS, 2012, 14 (01) :82-85

[7] Towards Safer Rocket Fuels: Hypergolic Imidazolylidene-Borane Compounds as Replacements for Hydrazine Derivatives [J].

Huang, Shi ;

Qi, Xiujuan ;

Liu, Tianlin ;

Wang, Kangcai ;

Zhang, Wenquan ;

Li, Jianlin ;

Zhang, Qinghua .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (29) :10187-10193

[8] Radical Reactions of N-Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles [J].

Kawamoto, Takuji ;

Geib, Steven J. ;

Curran, Dennis P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8617-8622

[9]

Kelley S.P., 2015, ALDRICHIM ACTA, V48, pel

[10] NHC-Boranes: Air- and Water-tolerant Co-initiators for Type II Photopolymerizations [J].

Lacote, Emmanuel ;

Curran, Dennis P. ;

Lalevee, Jacques .

CHIMIA, 2012, 66 (06) :382-385

← 1 2 3 →