Synthesis of 3-iodothiophenes via iodocyclization of (Z)-thiobutenynes

被引：28

作者：

Santana, Amanda S. ^{[1
,2
]}

Carvalho, Diego B. ^{[1
,2
]}

Cassemiro, Nadla S. ^{[1
,2
]}

Viana, Luiz H. ^{[1
,2
]}

Hurtado, Gabriela R. ^{[1
,2
]}

Amaral, Marcos S. ^{[1
,2
]}

Kassab, Najla M. ^{[1
,2
]}

Guerrero, Palimecio G., Jr. ^{[3
]}

Barbosa, Sandro L. ^{[4
]}

Dabdoub, Miguel J. ^{[5
]}

Baroni, Adriano C. M. ^{[1
,2
]}

机构：

[1] Univ Fed Mato Grosso do Sul, UFMS, Ctr Ciancias Biol & Saude, LASQUIM Lab Sintese & Quim Med, BR-79070900 Campo Grande, MS, Brazil

[2] Univ Fed Mato Grosso do Sul, UFMS, Inst Quim, BR-79070900 Campo Grande, MS, Brazil

[3] Univ Tecnol Fed Parana, UTFPR, DAQBi, Dept Quim & Biol, BR-80230901 Curitiba, PR, Brazil

[4] Univ Fed Vale Jequitinhonha & Mucuri, Dept Farm & Bioquim, BR-39100000 Diamantina, MG, Brazil

[5] Univ Sao Paulo, Dept Quim, BR-14040901 Ribeirao Preto, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 01期

关键词：

(Z)-Thiobutenynes; Iodocyclization; 3-Iodothiophenes; Sonogashira cross coupling; ONE-POT SYNTHESIS; ELECTROPHILIC CYCLIZATION; VINYLIC TELLURIDES; THIOPHENES; PRECURSORS;

D O I：

10.1016/j.tetlet.2013.10.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple synthesis of 3-iodothiophenes was demonstrated using a wide range of (Z)-thioenynes. The key step in the iodocyclofunctionalization was the selective reduction of the triple bond in (Z)-thioenynes by the addition of iodine as an electrophilic agent. The 3-iodothiophenes were obtained in good to excellent yields of 61-92%. The 3-iodothiophenes were used as substrates in Sonogashira cross-coupling reactions to obtain thiophene acetylenes. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：52 / 55

页数：4

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