Nickel-catalyzed and benzoic acid-promoted direct sulfenylation of unactivated arenes

被引:107
作者
Yang, Ke [1 ]
Wang, Yuqi [1 ]
Chen, Xinyong [1 ]
Kadi, Adnan A. [2 ]
Fun, Hoong-Kun [2 ]
Sun, Hao [1 ]
Zhang, Yan [1 ,2 ]
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 BOND; COUPLING REACTIONS; DIRECT THIOLATION; C(SP(3))-H BONDS; ARYL HALIDES; COPPER; FUNCTIONALIZATION; ACTIVATION; EFFICIENT; ARYLATION;
D O I
10.1039/c4cc10431e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A nickel-catalyzed and benzoic acid-promoted direct sulfenylation of unactivated arenes using removable 2-(pyridine-2-yl)-isopropylamine as a directing group is described. This strategy provides an efficient access to valuable aryl sulfides with ample substrate scope and a high degree of functional group tolerance.
引用
收藏
页码:3582 / 3585
页数:4
相关论文
共 80 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives [J].
Aihara, Yoshinori ;
Tobisu, Mamoru ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15509-15512
[3]   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
[4]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[5]   Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur [J].
Alcaraz, ML ;
Atkinson, S ;
Cornwall, P ;
Foster, AC ;
Gill, DM ;
Humphries, LA ;
Keegan, PS ;
Kemp, R ;
Merifield, E ;
Nixon, RA ;
Noble, AJ ;
O'Beirne, D ;
Patel, ZM ;
Perkins, J ;
Rowan, P ;
Sadler, P ;
Singleton, JT ;
Tornos, J ;
Watts, AJ ;
Woodland, IA .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (05) :555-569
[6]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[7]   Novel C-H functionalization of arenes: palladium-catalyzed synthesis of diaryl sulfides [J].
Anbarasan, Pazhamalai ;
Neumann, Helfried ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2011, 47 (11) :3233-3235
[8]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[9]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[10]   C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].
Chen, David Y. -K. ;
Youn, So Won .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474