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通过一锅 Sonogashira-Glaser 环化序列的伪五组分合成 2,5-二（杂）芳基噻吩。

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence.

机构信息

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany.

出版信息

Beilstein J Org Chem. 2011;7:1499-503. doi: 10.3762/bjoc.7.174. Epub 2011 Nov 4.

DOI:10.3762/bjoc.7.174
PMID:22238523
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3252849/
Abstract

Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.

摘要

基于连续一锅 Sonogashira-Glaser 偶联-环化序列，我们合成了多种 2,5-双（杂）芳基噻吩，产率中等至良好。该反应使用了单一的 Pd/Cu 催化剂体系，无需进一步添加催化剂，且使用了易得、稳定的起始原料，为标题化合物的合成提供了简洁、高效的途径。这种新型的从碘代（杂）芳烃出发的拟五组分合成方法特别适合作为直接合成具有明确结构的噻吩寡聚物的方法，而噻吩寡聚物在材料科学中具有特殊的应用价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/fba1d1c2ede1/Beilstein_J_Org_Chem-07-1499-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/9aaa464d1924/Beilstein_J_Org_Chem-07-1499-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/717fd86e6c18/Beilstein_J_Org_Chem-07-1499-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/ed7234a8898d/Beilstein_J_Org_Chem-07-1499-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/fba1d1c2ede1/Beilstein_J_Org_Chem-07-1499-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/9aaa464d1924/Beilstein_J_Org_Chem-07-1499-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/717fd86e6c18/Beilstein_J_Org_Chem-07-1499-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/ed7234a8898d/Beilstein_J_Org_Chem-07-1499-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d545/3252849/fba1d1c2ede1/Beilstein_J_Org_Chem-07-1499-g002.jpg

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