A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles

被引：137

作者：

Huang, Dayun ^{[1
]}

Chen, Jiuxi ^{[1
]}

Dan, Weixing ^{[1
]}

Ding, Jinchang ^{[1
,2
]}

Liu, Miaochang ^{[1
]}

Wu, Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Vocat & Tech Coll, Coll Light Ind, Wenzhou 325035, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

3-arylthioindoles; 2-bromo-3-arylthioindoles; bromosulfenylation; metal-free conditions; sulfenylation; EFFICIENT SULFENYLATION; CATALYZED SULFENYLATION; QUINONE MONO-O; S-ACETALS; POTENT INHIBITORS; 2ND SULFENYLATION; ARYL SULFONES; 3-SULFENYL; DISULFIDES; 3-SELENYLINDOLES; ARYLTHIOINDOLES;

D O I：

10.1002/adsc.201200227

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of C-S and C-Br bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.

引用

页码：2123 / 2128

页数：6

共 52 条

[1]

ATKINSON JG, 1988, SYNTHESIS-STUTTGART, P480

[2] Nucleophilic reactions in the indole series: displacement of bromine under phase transfer catalysis [J].

Barraja, Paola ;

Diana, Patrizia ;

Carbone, Anna ;

Cirrincione, Girolamo .

TETRAHEDRON, 2008, 64 (51) :11625-11631

[3] Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCVNS5B polymerase:: From benzimidazole to indole scaffolds [J].

Beaulieu, Pierre L. ;

Gillard, James ;

Bykowski, Darren ;

Brochu, Christian ;

Dansereau, Nathalie ;

Duceppe, Jean-Simon ;

Haché, Bruno ;

Jakalian, Araz ;

Lagacé, Lisette ;

LaPlante, Steven ;

McKercher, Ginette ;

Moreau, Elaine ;

Perreault, Stphane ;

Stammers, Timothy ;

Thauvette, Louise ;

Warrington, Jeff ;

Kukolj, George .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) :4987-4993

[4]

Bedford, 2011, ANGEW CHEM, V123, P5638

[5] Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].

Bedford, Robin B. ;

Haddow, Mairi F. ;

Mitchell, Charlotte J. ;

Webster, Ruth L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527

[6] PREPARATION AND DIELS-ALDER REACTIVITY OF SEVERAL NEW CHALCOGEN-HALOGEN SUBSTITUTED BUTADIENES [J].

BRIDGES, AJ ;

FISCHER, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :2954-2961

[7] A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA [J].

Campbell, JA ;

Broka, CA ;

Gong, L ;

Walker, KAM ;

Wang, JH .

TETRAHEDRON LETTERS, 2004, 45 (21) :4073-4075

[8] Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu4NI-Induced Electrophilic Cyclization [J].

Chen, Yu ;

Cho, Chul-Hee ;

Shi, Feng ;

Larock, Richard C. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) :6802-6811

[9] A Novel Synthetic Route to 3-Sulfenyl- and 3-Selenylindoles by n-BU4NI-Induced Electrophilic Cyclization [J].

Chen, Yu ;

Cho, Chul-Hee ;

Larock, Richard C. .

ORGANIC LETTERS, 2009, 11 (01) :173-176

[10] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis [J].

Crich, David ;

Banerjee, Abhisek .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) :151-161

← 1 2 3 4 5 6 →