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

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 goo...

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Published inTetrahedron letters Vol. 55; no. 1; pp. 52 - 55
Main Authors Santana, Amanda S., Carvalho, Diego B., Cassemiro, Nadla S., Viana, Luiz H., Hurtado, Gabriela R., Amaral, Marcos S., Kassab, Najla M., Guerrero, Palimécio G., Barbosa, Sandro L., Dabdoub, Miguel J., Baroni, Adriano C.M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2014
Elsevier
Subjects
(Z)-Thiobutenynes
3-Iodothiophenes
Chemistry
Chemistry, Organic
Iodocyclization
Physical Sciences
Science & Technology
Sonogashira cross coupling
3-Iodothiophenes
(Z)-Thiobutenynes
Iodocyclization
Sonogashira cross coupling
ELECTROPHILIC CYCLIZATION
ONE-POT SYNTHESIS
VINYLIC TELLURIDES
THIOPHENES
PRECURSORS
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.10.118