Cobalt-Catalyzed Decarboxylative 2-Benzoylation of Oxazoles and Thiazoles with α-Oxocarboxylic Acids

被引:67
作者
Yang, Ke [1 ]
Chen, Xinyong [1 ]
Wang, Yuqi [1 ]
Li, Wanqing [1 ]
Kadi, Adnan A. [2 ]
Fun, Hoong-Kun [2 ]
Sun, Hao [1 ]
Zhang, Yan [1 ,2 ]
Li, Guigen [1 ]
Lu, Hongjian [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China
[2] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; CARBON-CARBON BONDS; O-METHYL KETOXIMES; ORTHO-ACYLATION; DIRECT ARYLATION; BENZOIC-ACIDS; DESULFITATIVE ARYLATION; DIRECT C2-ALKYLATION; ARYLGLYOXYLIC ACIDS; AZOLES;
D O I
10.1021/acs.joc.5b01450
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cobalt-catalyzed decarboxylative cross-coupling of oxazoles and thiazoles with alpha-oxocarboxylic acids was developed through an sp(2) C-H bond functionalization process. This work represents the first example of cobalt-catalyzed decarboxylative C-H bond functionalization and provides an efficient means of building some important bioactive heteroaryl ketone derivatives.
引用
收藏
页码:11065 / 11072
页数:8
相关论文
共 50 条
[21]   Palladium-Catalyzed Decarboxylative Acylation of O-Phenyl Carbamates with -Oxocarboxylic Acids at Room Temperature [J].
Sharma, Satyasheel ;
Kim, Aejin ;
Park, Eonjeong ;
Park, Jihye ;
Kim, Minyoung ;
Kwak, Jong Hwan ;
Lee, Sang Hwi ;
Jung, Young Hoon ;
Kim, In Su .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) :667-672
[22]   Palladium-Catalyzed Primary Amine-Directed Decarboxylative Annulation of α-Oxocarboxylic Acids: Access to Indolo[1,2-a]quinazolines [J].
Jiang, Guangbin ;
Wang, Shoucai ;
Zhang, Jun ;
Yu, Jianwen ;
Zhang, Ziang ;
Ji, Fanghua .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1798-1802
[23]   A Highly Efficient Palladium-Catalyzed Decarboxylative ortho-Acylation of Azobenzenes with α-Oxocarboxylic Acids: Direct Access to Acylated Azo Compounds [J].
Li, Hongji ;
Li, Pinhua ;
Tan, Hui ;
Wang, Lei .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (43) :14432-14436
[24]   DMAP-Catalyzed Regel-Type Direct C-2 (Hetero)Aroylation of Oxazoles and Thiazoles Derivatives with Acid Chlorides [J].
Lassalas, Pierrik ;
Marsais, Francis ;
Hoarau, Christophe .
SYNLETT, 2013, 24 (17) :2233-2240
[25]   Bu4NI-catalyzed decarboxylative acyloxylation of an sp3 C-H bond adjacent to a heteroatom with α-oxocarboxylic acids [J].
Zhang, Shuai ;
Guo, Li-Na ;
Wang, Hua ;
Duan, Xin-Hua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (26) :4308-4311
[26]   Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with α-oxocarboxylic acids [J].
Wang, Cuiping ;
Wang, Shaoyan ;
Li, Hua ;
Yan, Jingbo ;
Chi, Haijun ;
Chen, Xichao ;
Zhang, Zhiqiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (11) :1721-1724
[27]   Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation [J].
Gong, Wei-Jie ;
Liu, De-Xian ;
Li, Fei-Long ;
Gao, Jun ;
Li, Hong-Xi ;
Lang, Jian-Ping .
TETRAHEDRON, 2015, 71 (08) :1269-1275
[28]   α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles [J].
Zhou, Liwei ;
Qiao, Shujia ;
Zhou, Fengru ;
Xuchen, Xinyu ;
Deng, Guobo ;
Yang, Yuan ;
Liang, Yun .
ORGANIC LETTERS, 2021, 23 (08) :2878-2883
[29]   Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles [J].
Dai, Ling ;
Yu, Shuling ;
Lv, Ningning ;
Ye, Xuanzeng ;
Shao, Yinlin ;
Chen, Zhongyan ;
Chen, Jiuxi .
ORGANIC LETTERS, 2021, 23 (15) :5664-5668
[30]   Cobalt-Catalyzed Oxidative Dimerization of 2-Phenylpyridine Derivatives [J].
Xie, Yanli ;
Xu, Dongdong ;
Sun, Wen-Wu ;
Zhang, Shi-Jin ;
Dong, Xiao-Ping ;
Liu, Bin ;
Zhou, Yingbi ;
Wu, Bin .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (08) :961-965