Palladium-Catalyzed Cross-Coupling of Arylboronic Acid and Benzonitriles Using DMSO as the Methylene Source

被引:20
作者
Ai, Han-Jun [1 ]
Qi, Xinxin [1 ]
Peng, Jin-Bao [1 ]
Ying, Jun [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
palladium; amides; DMSO; cross-coupling; methylene sources; METAL-FREE CONDITIONS; DIMETHYL-SULFOXIDE; CONVENIENT ACCESS; METHYLATION; IMIDAZOHETEROCYCLES; FORMYLATION; REAGENT; KETONES;
D O I
10.1002/ajoc.201800502
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An interesting strategy on palladium-catalyzed cross-coupling of arylboronic acids and benzonitriles has been developed. In this approach, DMSO was utilized as the methylene source and reacted with benzamides (generated insitu from benzonitriles) to form an N-acyliminium cation, followed by palladium-catalyzed cross-coupling with phenylboronic acids to afford the final products. A variety of the desired products were obtained in moderate to excellent yield.
引用
收藏
页码:2045 / 2048
页数:4
相关论文
共 44 条
[1]   Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen [J].
Cao, Hua ;
Lei, Sai ;
Li, Naiying ;
Chen, Longbin ;
Liu, Jingyun ;
Cai, Huiyin ;
Qiu, Shuxian ;
Tan, Jingwen .
CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1823-1825
[2]   Radical trideuteromethylation with deuterated dimethyl sulfoxide in the synthesis of heterocycles and labelled building blocks [J].
Caporaso, Roberta ;
Manna, Srimanta ;
Zinken, Sarah ;
Kochnev, Alexander R. ;
Lukyanenko, Evgeny R. ;
Kurkin, Alexander V. ;
Antonchick, Andrey P. .
CHEMICAL COMMUNICATIONS, 2016, 52 (84) :12486-12489
[3]   DIMETHYLSULFOXONIUM METHYLIDE [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :867-&
[4]   One-pot three-component synthesis of quinazolines via a copper-catalysed oxidative amination reaction [J].
Duan, Tiantian ;
Zhai, Tianran ;
Liu, Huanhuan ;
Yan, Zilong ;
Zhao, Yue ;
Feng, Lei ;
Ma, Chen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (27) :6561-6567
[5]   Nickel and Copper-Catalyzed Carbonylation Reaction of Organoboranes [J].
Etemadi-Davan, Elham ;
Iranpoor, Nasser ;
Arshad, Pourya .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (04) :683-687
[6]   The ammonium-promoted formylation of indoles by DMSO and H2O [J].
Fei, Haiyang ;
Yu, Jintao ;
Jiang, Yan ;
Guo, Huan ;
Cheng, Jiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (41) :7092-7095
[7]   Oxidative Annulations Involving DMSO and Formamide: K2S2O8 Mediated Syntheses of Quinolines and Pyrimidines [J].
Jadhav, Santosh D. ;
Singh, Anand .
ORGANIC LETTERS, 2017, 19 (20) :5673-5676
[8]   Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source [J].
Jia, Jing ;
Jiang, Qing ;
Zhao, An ;
Xu, Bin ;
Liu, Qiang ;
Luo, Wei-Ping ;
Guo, Can-Cheng .
SYNTHESIS-STUTTGART, 2016, 48 (03) :421-428
[9]   Dimethyl Sulfoxide as a Synthon in Organic Chemistry [J].
Jones-Mensah, Ebenezer ;
Karki, Megha ;
Magolan, Jakob .
SYNTHESIS-STUTTGART, 2016, 48 (10) :1421-1436
[10]  
Katritzky A. R., 2014, ADV HETEROCYCLIC CHE