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用于铜介导的芳基三氟甲基化和五氟乙基化反应的碳-碳键裂解

Carbon-carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations.

作者信息

Sugiishi Tsuyuka, Amii Hideki, Aikawa Kohsuke, Mikami Koichi

机构信息

Division of Molecular Science, Faculty of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan.

出版信息

Beilstein J Org Chem. 2015 Dec 18;11:2661-70. doi: 10.3762/bjoc.11.286. eCollection 2015.

DOI:10.3762/bjoc.11.286
PMID:26734112
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4685791/
Abstract

This short review highlights the copper-mediated fluoroalkylation using perfluoroalkylated carboxylic acid derivatives. Carbon-carbon bond cleavage of perfluoroalkylated carboxylic acid derivatives takes place in fluoroalkylation reactions at high temperature (150-200 °C) or under basic conditions to generate fluoroalkyl anion sources for the formation of fluoroalkylcopper species. The fluoroalkylation reactions, which proceed through decarboxylation or tetrahedral intermediates, are useful protocols for the synthesis of fluoroalkylated aromatics.

摘要

本短文重点介绍了使用全氟烷基化羧酸衍生物的铜介导氟烷基化反应。在高温（150 - 200°C）或碱性条件下，全氟烷基化羧酸衍生物的碳 - 碳键在氟烷基化反应中发生断裂，生成氟烷基阴离子源以形成氟烷基铜物种。通过脱羧或四面体中间体进行的氟烷基化反应，是合成氟烷基化芳烃的有用方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/46294eb8ba86/Beilstein_J_Org_Chem-11-2661-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/1b5941ade51e/Beilstein_J_Org_Chem-11-2661-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/79e0618d4803/Beilstein_J_Org_Chem-11-2661-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/2e58f8082f4c/Beilstein_J_Org_Chem-11-2661-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/a77500bbfe93/Beilstein_J_Org_Chem-11-2661-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/501a3a3972f3/Beilstein_J_Org_Chem-11-2661-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/319bcfa196b1/Beilstein_J_Org_Chem-11-2661-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/b1982261098c/Beilstein_J_Org_Chem-11-2661-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/884cb9512ef2/Beilstein_J_Org_Chem-11-2661-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/46294eb8ba86/Beilstein_J_Org_Chem-11-2661-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/1b5941ade51e/Beilstein_J_Org_Chem-11-2661-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/79e0618d4803/Beilstein_J_Org_Chem-11-2661-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/2e58f8082f4c/Beilstein_J_Org_Chem-11-2661-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/a77500bbfe93/Beilstein_J_Org_Chem-11-2661-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/501a3a3972f3/Beilstein_J_Org_Chem-11-2661-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/319bcfa196b1/Beilstein_J_Org_Chem-11-2661-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/b1982261098c/Beilstein_J_Org_Chem-11-2661-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/884cb9512ef2/Beilstein_J_Org_Chem-11-2661-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5bd6/4685791/46294eb8ba86/Beilstein_J_Org_Chem-11-2661-g018.jpg

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