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以2-三氟甲基苯并咪唑啉作为三氟甲基化试剂对碘芳烃进行催化三氟甲基化反应。

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent.

作者信息

Uchikura Tatsuhiro, Kamiyama Nanami, Ishikawa Taisuke, Akiyama Takahiko

机构信息

Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.

出版信息

Beilstein J Org Chem. 2020 Sep 30;16:2442-2447. doi: 10.3762/bjoc.16.198. eCollection 2020.

DOI:10.3762/bjoc.16.198
PMID:33082878
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7537379/
Abstract

The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)-CF species is the rate-determining step.

摘要

通过使用2-三氟甲基苯并咪唑啉衍生物作为三氟甲基化试剂,并在作为配体的2,2'-联吡啶存在下加入催化量的Cu(I),实现了碘代芳烃的三氟甲基化。通过机理研究,我们发现碘代芳烃向Cu(I)-CF物种的氧化加成是速率决定步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/4613fc66706e/Beilstein_J_Org_Chem-16-2442-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/979b7759eec7/Beilstein_J_Org_Chem-16-2442-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/84fdfb54b902/Beilstein_J_Org_Chem-16-2442-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/6bfe06e6c1a5/Beilstein_J_Org_Chem-16-2442-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/c5b98930edf2/Beilstein_J_Org_Chem-16-2442-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/4613fc66706e/Beilstein_J_Org_Chem-16-2442-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/979b7759eec7/Beilstein_J_Org_Chem-16-2442-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/84fdfb54b902/Beilstein_J_Org_Chem-16-2442-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/6bfe06e6c1a5/Beilstein_J_Org_Chem-16-2442-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/c5b98930edf2/Beilstein_J_Org_Chem-16-2442-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/80d9/7537379/4613fc66706e/Beilstein_J_Org_Chem-16-2442-g006.jpg

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本文引用的文献

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