Synthesis of Thieno-Fused Heterocycles through Reiterative Iodocyclization

Iodocyclization of ethynyl methyl sulfides gives 3‐iodo‐2‐thiomethyl heterocycles, setting up the synthesis of thieno‐fused systems through a subsequent iteration of alkyne coupling and iodocylization. This approach can also be exploited in the synthesis of polyfused thiophenes. In developing this p...

Full description

Saved in:

Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 356; no. 9; pp. 1974 - 1978
Main Authors:	Aurelio, Luigi, Volpe, Rohan, Halim, Rosliana, Scammells, Peter J., Flynn, Bernard L.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 16-06-2014 WILEY‐VCH Verlag
Subjects:	Alkynes Bias Catalysis cyclization Electronics iodocyclization Joining Sulfides sulfur heterocycles Synthesis synthetic methods Thiophenes
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	Iodocyclization of ethynyl methyl sulfides gives 3‐iodo‐2‐thiomethyl heterocycles, setting up the synthesis of thieno‐fused systems through a subsequent iteration of alkyne coupling and iodocylization. This approach can also be exploited in the synthesis of polyfused thiophenes. In developing this protocol it was necessary to address issues associated with unfavourable electronic bias and redox sensitivity in some substrates. The manner in which these have been addressed should prove useful elsewhere in iodocyclization chemisty.
Bibliography:	ArticleID:ADSC201400072 ark:/67375/WNG-F2RRR7WQ-6 istex:22F90506553FF020D2625F84F77CB05D122937D2 ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.201400072