Electronic Effects on Chiral NHC-Transition-Metal Catalysis

被引:13
作者
Yong, Xuefeng [1 ,2 ]
Thurston, Ryan [1 ,3 ]
Ho, Chun-Yu [1 ]
机构
[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Peoples R China
[2] Harbin Inst Technol, Sch Chem & Chem Engn, Harbin, Heilongjiang, Peoples R China
[3] Friedrich Alexander Univ Erlangen Nurnberg, Dept Chem & Pharm, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany
来源
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 10期
关键词
electronic effect; chiral N-heterocyclic carbenes; transition-metal catalysis; enantioselective synthesis; N-HETEROCYCLIC CARBENE; BUCHWALD-HARTWIG AMINATION; ETHER-PHOSPHANE LIGANDS; BASIC LIGANDS; METHANOL CARBONYLATION; PALLADIUM COMPLEXES; PYRIDINE MOIETY; ASYMMETRIC HYDROGENATION; COORDINATION CHEMISTRY; MONOPHOSPHINE LIGANDS;
D O I
10.1055/s-0037-1611751
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Though the properties of N-heterocyclic carbenes (NHCs) are generally dominated by the very strong sigma donating character, electronic activation has emerged as an effective method to cooperate with typical carbon-framework steric optimization for highly enantioselective chiral NHC-transition-metal catalysis in recent years. NHC electronic changes associated with structural variations are now better understood by quantitative analysis using various methods. Here we highlighted and correlated some interesting chiral induction improvement methods, which were brought by electronic and steric cooperation on chiral NHC-transition-metal catalysis.
引用
收藏
页码:2058 / 2080
页数:23
相关论文
共 141 条
[1]   Application of a C2-Symmetric Copper Carbenoid in the Enantioselective Hydrosilylation of Dialkyl and Aryl-Alkyl Ketones [J].
Albright, Abigail ;
Gawley, Robert E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19680-19683
[2]   Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids [J].
Albright, Abigail ;
Eddings, Daniel ;
Black, Regina ;
Welch, Christopher J. ;
Gerasimchuk, Nikolay N. ;
Gawley, Robert E. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) :7341-7351
[3]   Imidazo[1,5-a]pyridine:: A versatile architecture for stable N-heterocyclic carbenes [J].
Alcarazo, M ;
Roseblade, SJ ;
Cowley, AR ;
Fernández, R ;
Brown, JM ;
Lassaletta, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3290-3291
[4]  
Alder R.W., 1999, Chem. Commun, V241
[5]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[6]   An air stable carbene and mixed carbene "dimers" [J].
Arduengo, AJ ;
Davidson, F ;
Dias, HVR ;
Goerlich, JR ;
Khasnis, D ;
Marshall, WJ ;
Prakasha, TK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12742-12749
[7]  
ARNOLD PL, 2001, CHEM COMMUN, V2340
[8]   Synthesis, Structures and Properties of Half-Sandwich Nickel(II) Complexes with Backbone-Modified NHC Ligands [J].
Banach, Lukasz ;
Gunka, Piotr A. ;
Gorska, Dominika ;
Podlewska, Maja ;
Zachara, Janusz ;
Buchowicz, Wlodzimierz .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2015, (34) :5677-5686
[9]   N-heterocyclic carbenes. 49. Chiral N-heterocyclic carbenes with restricted flexibility in asymmetric catalysis [J].
Baskakov, Denys ;
Herrmann, Wolfgang A. ;
Herdtweck, Eberhardt ;
Hoffmann, Stephan D. .
ORGANOMETALLICS, 2007, 26 (03) :626-632
[10]   Imidazol-2-ylidene-4-olate: an anionic N-heterocyclic carbene pre-programmed for further derivatization [J].
Benhamou, Laure ;
Cesar, Vincent ;
Gornitzka, Heinz ;
Lugan, Noel ;
Lavigne, Guy .
CHEMICAL COMMUNICATIONS, 2009, (31) :4720-4722