Selective approach to thioesters and thioethers via sp3 C-H activation of methylarenes

被引：29

作者：

Feng, J. ^{[1
]}

Lu, G. -P. ^{[1
]}

Cai, C. ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 97期

关键词：

ONE-POT SYNTHESIS; CROSS-COUPLING REACTIONS; N BOND FORMATION; THIOL ESTERS; OXIDATIVE ESTERIFICATION; CATALYZED SYNTHESIS; DIRECTING GROUP; CARBOXYLIC-ACIDS; IONIC LIQUID; ARYL HALIDES;

D O I：

10.1039/c4ra09450f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel C-S cross-dehydrogenative coupling (CDC) approaches for the selective synthesis of thioesters and thioethers have been developed via sp(3) C-H activation of methylarenes and subsequent functionalization. The reaction of methylarenes with thiols resulted in thioesters in the presence of a FeBr2/TBHP system, while treatment of methylarenes with thiols in the Pd(OAc)(2)/O-2/TBHP system led to the formation of thioethers. Both the green protocols demonstrate good functional group tolerance and satisfactory yields.

引用

页码：54409 / 54415

页数：7

共 114 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] Thioesterification of Alkylbenzenes with Thiols via Copper-Catalyzed Cross-Dehydrogenative Coupling without a Directing Group [J].

Ali, Wajid ;

Guin, Srimanta ;

Rout, Saroj Kumar ;

Gogoi, Anupal ;

Patel, Bhisma K. .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :3099-3105

[3]

[Anonymous], 2010, C H ACTIVATION

[4] Intermolecular oxidative cross-coupling of arenes [J].

Ashenhurst, James A. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548

[5] Synthesis of Acylsilanes by Palladium-catalyzed Cross-coupling Reaction of Thiol Esters and Silylzinc Chlorides [J].

Azuma, Hiroki ;

Okano, Kentaro ;

Tokuyama, Hidetoshi .

CHEMISTRY LETTERS, 2011, 40 (09) :959-961

[6] Silica-promoted facile synthesis of thioesters and thioethers: a highly efficient, reusable and environmentally safe solid support [J].

Basu, Basudeb ;

Paul, Susmita ;

Nanda, Ashis K. .

GREEN CHEMISTRY, 2010, 12 (05) :767-771

[7] Catechol violet as new, efficient, and versatile ligand for Cu(I)-catalyzed C-S coupling reactions [J].

Basu, Basudeb ;

Mandal, Bablee ;

Das, Sajal ;

Kundu, Sekhar .

TETRAHEDRON LETTERS, 2009, 50 (39) :5523-5528

[8] Copper-Catalyzed Domino Oxidation-Acyloxylation Reaction of 2-Arylpyridines with Aldehydes or Methylarenes [J].

Bian, Yong-Jun ;

Xiang, Chang-Bing ;

Chen, Zhi-Ming ;

Huang, Zhi-Zhen .

SYNLETT, 2011, (16) :2407-2409

[9] Mechanistic Study of the Oxidative Coupling of Styrene with 2-Phenylpyridine Derivatives Catalyzed by Cationic Rhodium(III) via C-H Activation [J].

Brasse, Mikael ;

Campora, Juan ;

Ellman, Jonathan A. ;

Bergman, Robert G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (17) :6427-6430

[10]

Burhardt M. N., J ORG CHEM, DOI [10.1021/jo5009965, DOI 10.1021/J05009965]

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