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溴代硒吩在钯催化直接芳基化反应中的反应活性。

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations.

作者信息

Skhiri Aymen, Ben Salem Ridha, Soulé Jean-François, Doucet Henri

机构信息

Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.

Laboratoire de Laboratoire de Chimie Organique LR 17ES08, Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, Tunisia.

出版信息

Beilstein J Org Chem. 2017 Dec 22;13:2862-2868. doi: 10.3762/bjoc.13.278. eCollection 2017.

DOI:10.3762/bjoc.13.278
PMID:29564014
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5753141/
Abstract

The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylated) selenophenes in high yields using both thiazole and thiophene derivatives. Moreover, sequential catalytic C2 heteroarylation, bromination, catalytic C5 arylation reactions allowed the synthesis of unsymmetrical 2,5-di(hetero)arylated selenophene derivatives in three steps from selenophene.

摘要

研究了2-溴代和2,5-二溴代硒吩在钯催化直接杂芳基化反应中的反应活性。对于2-溴代硒吩，只有反应活性最高的杂芳烃可用于制备2-杂芳基化硒吩；而2,5-二溴代硒吩通常使用噻唑和噻吩衍生物都能高产率地得到2,5-二（杂芳基化）硒吩。此外，通过连续的催化C2杂芳基化、溴化、催化C5芳基化反应，可以从硒吩分三步合成不对称的2,5-二（杂）芳基化硒吩衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/94a5e937502e/Beilstein_J_Org_Chem-13-2862-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/bb983c605125/Beilstein_J_Org_Chem-13-2862-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/7fc8d9e0ea47/Beilstein_J_Org_Chem-13-2862-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/7a845ba995d4/Beilstein_J_Org_Chem-13-2862-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/88f6d255a3fe/Beilstein_J_Org_Chem-13-2862-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/94a5e937502e/Beilstein_J_Org_Chem-13-2862-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/bb983c605125/Beilstein_J_Org_Chem-13-2862-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/7fc8d9e0ea47/Beilstein_J_Org_Chem-13-2862-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/7a845ba995d4/Beilstein_J_Org_Chem-13-2862-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/88f6d255a3fe/Beilstein_J_Org_Chem-13-2862-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32d9/5753141/94a5e937502e/Beilstein_J_Org_Chem-13-2862-g006.jpg

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