Carbene-stabilized main group radicals and radical ions

被引:392
作者
Martin, Caleb D. [1 ]
Soleilhavoup, Michele [1 ]
Bertrand, Guy [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, Joint CNRS UCSD Res Lab UMI 3555, La Jolla, CA 92093 USA
关键词
N-HETEROCYCLIC CARBENE; ELECTRON-PARAMAGNETIC-RESONANCE; TRANSITION-METAL-COMPLEXES; PINCER DICARBENE COMPLEXES; ALKYL AMINO CARBENES; PHOSPHORUS-CONTAINING RADICALS; STABLE NUCLEOPHILIC CARBENE; BORON TRIPLE BOND; IN-THE-BOX; PI-ACCEPTOR;
D O I
10.1039/c3sc51174j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Shortly after their discovery at the end of the 80s, stable singlet carbenes have been recognized as excellent ligands for transition metal based catalysts, and as organo-catalysts in their own right. At the end of the 2000s, it has been shown that they can coordinate main group elements in their zero oxidation state, and even activate small molecules. This review covers examples in the literature dealing with the most recent application of stable singlet carbenes, namely their use to stabilize radicals and radical ions that are otherwise unstable.
引用
收藏
页码:3020 / 3030
页数:11
相关论文
共 180 条
[1]   Nucleophilic carbene complexes of manganocene [J].
Abernethy, CD ;
Cowley, AH ;
Jones, RA ;
Macdonald, CLB ;
Shukla, P ;
Thompson, LK .
ORGANOMETALLICS, 2001, 20 (17) :3629-3631
[2]   Oxidation of Carbene-Stabilized Diarsenic: Diarsene Dications and Diarsenic Radical Cations [J].
Abraham, Mariham Y. ;
Wang, Yuzhong ;
Xie, Yaoming ;
Gilliard, Robert J., Jr. ;
Wei, Pingrong ;
Vaccaro, Brian J. ;
Johnson, Michael K. ;
Schaefer, Henry F., III ;
Schleyer, Paul v. R. ;
Robinson, Gregory H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (07) :2486-2488
[3]   Carbene Stabilization of Diarsenic: From Hypervalency to Allotropy [J].
Abraham, Mariham Y. ;
Wang, Yuzhong ;
Xie, Yaoming ;
Wei, Pingrong ;
Schaefer, Henry F., III ;
Schleyer, P. von R. ;
Robinson, Gregory H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (02) :432-435
[4]   An isolable and monomeric phosphorus radical that is resonance-stabilized by the vanadium(IV/V) redox couple [J].
Agarwal, Paresh ;
Piro, Nicholas A. ;
Meyer, Karsten ;
Mueller, Peter ;
Cummins, Christopher C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3111-3114
[5]   Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis [J].
Alcarazo, Manuel ;
Stork, Timon ;
Anoop, Anakuthil ;
Thiel, Walter ;
Fuerstner, Alois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (14) :2542-2546
[6]   Synthesis and Characterization of B-Heterocyclic π-Radical and Its Reactivity as a Boryl Radical [J].
Aramaki, Yoshitaka ;
Orniya, Hideki ;
Yamashita, Makoto ;
Nakabayashi, Koji ;
Ohkoshi, Shin-ichi ;
Nozaki, Kyoko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (49) :19989-19992
[7]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[8]   A STABLE DIAMINOCARBENE [J].
ARDUENGO, AJ ;
GOERLICH, JR ;
MARSHALL, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11027-11028
[9]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[10]  
Armstrong A, 2006, ACS SYM SER, V917, P66