Synthesis of Dibenzothiophenes by Pd-Catalyzed Dual C-H Activation from Diaryl Sulfides

被引：62

作者：

Che, Rui ^{[1
]}

Wu, Zhiqing ^{[1
]}

Li, Zhengkai ^{[1
]}

Xiang, Haifeng ^{[1
]}

Zhou, Xiangge ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Chengdu 610064, Peoples R China

[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 24期

关键词：

C-H arylation; cyclization; dibenzothiophenes; diphenyl sulfides; palladium; FIELD-EFFECT TRANSISTORS; TRANSITION-METAL-COMPLEXES; DEHYDROGENATIVE CYCLIZATION; BOND FUNCTIONALIZATIONS; ORGANIC SEMICONDUCTORS; FLUORENE DERIVATIVES; DIRECT ARYLATION; N-ARYLATION; MECHANISM; CARBAZOLES;

D O I：

10.1002/chem.201402265

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed dual C-H functionalization of diaryl sulfides to form dibenzothiophenes (DBTs) by oxidative dehydrogenative cyclization is reported. This protocol afforded various DBTs in moderate to good yields with tolerance of a wide variety of substrates. Benzo[1,2-b:4,5-b']bis[b] benzothiophene was successfully synthesized by this method, which was used as an organic semiconductor for field-effect transistors.

引用

页码：7258 / 7261

页数：4

共 50 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] BIS-BASIC-SUBSTITUTED POLYCYCLIC AROMATIC-COMPOUNDS - NEW CLASS OF ANTIVIRAL AGENTS .8. BIS-BASIC DERIVATIVES OF CARBAZOLE, DIBENZOFURAN, AND DIBENZOTHIOPHENE [J].

ALBRECHT, WL ;

FLEMING, RW ;

HORGAN, SW ;

MAYER, GD .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (03) :364-371

[3]

Allard S., 2008, Angew. Chem, V120, P4138, DOI DOI 10.1002/ANGE.200701920

[4] Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].

Allard, Sybille ;

Forster, Michael ;

Souharce, Benjamin ;

Thiem, Heiko ;

Scherf, Ullrich .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098

[5]

[Anonymous], 2011, ANGEW CHEM, V123, P5323

[6]

[Anonymous], 2006, J AM CHEM SOC, V128, P16496

[7]

[Anonymous], 1990, CHEM REV, V90, P403

[8]

[Anonymous], 2013, ANGEW CHEM-GER EDIT

[9] Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions [J].

Black, Michael ;

Cadogan, J. I. G. ;

McNab, Hamish .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) :2961-2967

[10] 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

← 1 2 3 4 5 →