Rhodium-catalyzed Direct Coupling of Benzothioamides with Alkenes and Alkynes through Directed C-H Bond Cleavage

被引：57
|
作者：
Yokoyama, Yuki [1 ]
Unoh, Yuto [1 ,2 ]
Bohmann, Rebekka Anna [1 ,3 ]
Satoh, Tetsuya [1 ,2 ,4 ]
Hirano, Koji [1 ]
Bolm, Carsten [3 ]
Miura, Masahiro [1 ]
机构：
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] ACT C, JST, Kawaguchi, Saitama 3320012, Japan
[3] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[4] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan
来源：
CHEMISTRY LETTERS | 2015年 / 44卷 / 08期
关键词：
OXIDATIVE ANNULATION; DIRECT ARYLATION; ALKENYLATION; SULFOXIDES; SULFOXIMINES; ACTIVATION; THIOETHERS; FUNCTIONALIZATIONS; OLEFINATION; INHIBITORS;
D O I：
10.1246/cl.150444
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Rhodium-catalyzed direct coupling of benzothioamides with alkenes proceeds smoothly involving ortho-C-H bond cleavage. The thioamides also couple with alkynes under similar conditions accompanied by desulfurization and C-N bond cleavage to produce indenone derivatives.
引用
收藏
页码：1104 / 1106
页数：3
相关论文
共 50 条
  • [31] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
    Colby, Denise A.
    Bergman, Robert G.
    Ellman, Jonathan A.
    CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
  • [32] Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C-H Bond with CO and Alcohols
    Guan, Zheng-Hui
    Ren, Zhi-Hui
    Spinella, Stephen M.
    Yu, Shichao
    Liang, Yong-Min
    Zhang, Xumu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) : 729 - 733
  • [33] Rhodium-Catalyzed Alkenylation of C-H Bonds in Aromatic Amides with Alkynes
    Shibata, Kaname
    Natsui, Satoko
    Chatani, Naoto
    ORGANIC LETTERS, 2017, 19 (09) : 2234 - 2237
  • [34] Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation
    Wang, Liang
    Wu, Wenting
    Chen, Qun
    He, Mingyang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (40) : 7923 - 7926
  • [35] Rhodium(III)-Catalyzed Ortho-Alkenylation through C-H Bond Cleavage Directed by Sulfoxide Groups
    Nobushige, Kazunori
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ORGANIC LETTERS, 2014, 16 (04) : 1188 - 1191
  • [36] Rhodium-Catalyzed Selective C-H Bond Functionalization of Quinolines
    Dhiman, Ankit K.
    Thakur, Ankita
    Kumar, Rakesh
    Sharma, Upendra
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1502 - 1518
  • [37] Rhodium-catalyzed triazole-directed C-H bond functionalization of arenes with diazo compounds
    Wang, Huanhong
    Yi, Xiaofei
    Cui, Yanli
    Chen, Wanzhi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (43) : 8191 - 8195
  • [38] Synthetic applications of rhodium-catalyzed imine-directed C-H bond activation.
    Wilson, RM
    Bergman, RG
    Ellman, JA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U337 - U337
  • [39] Direct carboxylation of simple arenes with CO2 through a rhodium-catalyzed C-H bond activation
    Suga, Takuya
    Mizuno, Hajime
    Takaya, Jun
    Iwasawa, Nobuharu
    CHEMICAL COMMUNICATIONS, 2014, 50 (92) : 14360 - 14363
  • [40] Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage
    Ueura, Kenji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14): : 5362 - 5367
12345