Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes from o-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process

被引：20

作者：

Zhang, Xiaoyun ^{[1
]}

Zeng, Weilan ^{[1
]}

Yang, Yuan ^{[1
]}

Huang, Hui ^{[1
]}

Liang, Yun ^{[1
,2
]}

机构：

[1] Hunan Normal Univ, Natl & Local Joint Engn Lab New Petrochem Mat & F, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China

[2] Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

来源：

SYNLETT | 2013年 / 24卷 / 13期

关键词：

transition-metal-free; benzo[b]thiophenes; o-halovinylbenzenes; direct SNAr-type reaction; cyclization; dehydrogenation process; ONE-POT SYNTHESIS; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; DERIVATIVES; THIOPHENES; BENZOTHIOPHENES; INHIBITORS;

D O I：

10.1055/s-0033-1339289

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes are provided in the high yields in the absence of a transition-metal catalyst.

引用

页码：1687 / 1692

页数：6

共 5 条

[1] Transition-Metal-Free Thiolation Annulation of 2-Fluorophenylacetylene Derivatives: Expedient Synthesis of Benzo[b] thiophenes Using Na2S•9H2O
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CHEMISTRYSELECT, 2016, 1 (05): : 1092 - 1095
[2] Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions
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[3] Transition-Metal-Free Synthesis of C-Glycosylated Phenanthridines via K2S2O8-Mediated Oxidative Radical Decarboxylation of Uronic Acids
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[4] Transition-Metal-Free Synthesis of Imidazo[2,1-b]thiazoles and Thiazolo[3,2-a]benzimidazoles via an S-Propargylation/5-exo-dig Cyclization/lsomerization Sequence Using Propargyl Tosylates as Substrates
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[5] K2S2O8-mediated metal-free direct P-H/C-H functionalization: a convenient route to benzo[b]phosphole oxides from unactivated alkynes
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