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

被引：58

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

页码：1104 / 1106

页数：3

共 52 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]

Agnimonhan F. H., 2012, Journal of Applied Pharmaceutical Science, V2, P62

[3] PNEUMOTOXIC EFFECTS OF THIOBENZAMIDE DERIVATIVES [J].

CASHMAN, JR ;

TRAIGER, GJ ;

HANZLIK, RP .

TOXICOLOGY, 1982, 23 (01) :85-93

[4] Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions [J].

Castro, Luis C. Misal ;

Chatani, Naoto .

CHEMISTRY LETTERS, 2015, 44 (04) :410-421

[5] Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions [J].

Cheng, Ying ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12349-12352

[6] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[7] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[8] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[9] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

[10] Hydroarylations of Heterobicyclic Alkenes through Rhodium-Catalyzed Directed C-H Functionalizations of S-Aryl Sulfoximines [J].

Dong, Wanrong ;

Parthasarathy, Kanniyappan ;

Cheng, Ying ;

Pan, Fangfang ;

Bolm, Carsten .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (48) :15732-15736

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