Catalytic C-C bond forming transformations via direct β-C-H functionalization of carbonyl compounds

被引:88
作者
Huang, Zhongxing [1 ]
Dong, Guangbin [1 ]
机构
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
关键词
C-H functionalization; Carbonyl compounds; beta-C-H bonds; C-C bond formation; UNACTIVATED C(SP(3))-H BONDS; KETO-ESTERS; STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR ARYLATION; ACTIVATION; AMINO; ALDEHYDES; ALKYLATION; SP(2); OLEFINATION;
D O I
10.1016/j.tetlet.2014.09.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Strategies have emerged over the past decade to enable the direct functionalization of the remote and inert beta-C-H bonds of carbonyl compounds. Based on these strategies, a wide collection of novel beta-C-C bond formation transformations have been developed, including arylation, alkylation, alkenylation, alkynylation, and carbonylation. This review summarizes these recent methods for C-C bond formations via direct beta-C-H functionalization of carbonyl compounds. The scope and limitation of each strategy are also discussed. (C) 2014 Elsevier Ltd. This is an open access article under the CC BY-NC-ND license.
引用
收藏
页码:5869 / 5889
页数:21
相关论文
共 66 条
[1]   Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901
[2]   Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986
[3]   Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones [J].
Aspin, Sam ;
Lopez-Suarez, Laura ;
Larini, Paolo ;
Goutierre, Anne-Sophie ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ORGANIC LETTERS, 2013, 15 (19) :5056-5059
[4]   Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds [J].
Aspin, Sam ;
Goutierre, Anne-Sophie ;
Larini, Paolo ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10808-10811
[5]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[6]  
Buckle D.R., 1991, COMPREHENSIVE ORGANI, V7, P119
[7]   Pd(II)-catalyzed alkylation of unactivated C(sp3)-H bonds: efficient synthesis of optically active unnatural α-amino acids [J].
Chen, Kai ;
Hu, Fang ;
Zhang, Shuo-Qing ;
Shi, Bing-Feng .
CHEMICAL SCIENCE, 2013, 4 (10) :3906-3911
[8]   Organocatalysis by N-heterocyclic, carbenes [J].
Enders, Dieter ;
Niemeier, Oliver ;
Henseler, Alexander .
CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655
[9]   Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions [J].
Engle, Keary M. ;
Mei, Tian-Sheng ;
Wasa, Masayuki ;
Yu, Jin-Quan .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :788-802
[10]   Facile Benzo-Ring Construction via Palladium-Catalyzed Functionalization of Unactivated sp3 C-H Bonds under Mild Reaction Conditions [J].
Feng, Yiqing ;
Wang, Yuji ;
Landgraf, Bradley ;
Liu, Shi ;
Chen, Gong .
ORGANIC LETTERS, 2010, 12 (15) :3414-3417