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高价碘(III)介导的叔碳和苄基碳中心的脱羧乙酰氧基化反应。

Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers.

作者信息

Kiyokawa Kensuke, Okumatsu Daichi, Minakata Satoshi

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

出版信息

Beilstein J Org Chem. 2018 May 15;14:1046-1050. doi: 10.3762/bjoc.14.92. eCollection 2018.

DOI:10.3762/bjoc.14.92
PMID:29977378
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6009488/
Abstract

The decarboxylative acetoxylation of carboxylic acids using a combination of PhI(OAc) and I in a CHCl/AcOH mixed solvent is reported. The reaction was successfully applied to two types of carboxylic acids containing an α-quaternary and a benzylic carbon center under mild reaction conditions. The resulting acetates were readily converted into the corresponding alcohols by hydrolysis.

摘要

报道了在CHCl₃/AcOH混合溶剂中使用PhI(OAc)₂和I的组合对羧酸进行脱羧乙酰氧基化反应。该反应在温和的反应条件下成功应用于含有α-季碳和苄基碳中心的两类羧酸。所得的乙酸酯通过水解很容易转化为相应的醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/2f57a4bd56b9/Beilstein_J_Org_Chem-14-1046-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/ded723caa429/Beilstein_J_Org_Chem-14-1046-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/0facfb0f7f16/Beilstein_J_Org_Chem-14-1046-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/f11614f30dce/Beilstein_J_Org_Chem-14-1046-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/6cd8224d330b/Beilstein_J_Org_Chem-14-1046-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/2f57a4bd56b9/Beilstein_J_Org_Chem-14-1046-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/ded723caa429/Beilstein_J_Org_Chem-14-1046-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/0facfb0f7f16/Beilstein_J_Org_Chem-14-1046-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/f11614f30dce/Beilstein_J_Org_Chem-14-1046-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/6cd8224d330b/Beilstein_J_Org_Chem-14-1046-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5e6/6009488/2f57a4bd56b9/Beilstein_J_Org_Chem-14-1046-g006.jpg

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1
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J Am Chem Soc. 2017 Nov 8;139(44):15632-15635. doi: 10.1021/jacs.7b09802. Epub 2017 Oct 30.
2
Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement.光诱导、铜催化脱羧 C-N 偶联生成保护胺:Curtius 重排的替代方法。
J Am Chem Soc. 2017 Sep 6;139(35):12153-12156. doi: 10.1021/jacs.7b07546. Epub 2017 Aug 25.
3
Copper-Catalyzed Decarboxylative Radical Silylation of Redox-Active Aliphatic Carboxylic Acid Derivatives.
铜催化的氧化还原活性脂肪族羧酸衍生物的脱羧基自由基硅化反应。
Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11649-11652. doi: 10.1002/anie.201706611. Epub 2017 Aug 10.
4
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.无过渡金属脱羧碘化:脱羧氧化交叉偶联的新途径。
J Am Chem Soc. 2017 Aug 23;139(33):11527-11536. doi: 10.1021/jacs.7b05155. Epub 2017 Aug 8.
5
Photoinduced decarboxylative borylation of carboxylic acids.光诱导羧酸的脱羧硼化反应。
Science. 2017 Jul 21;357(6348):283-286. doi: 10.1126/science.aan3679. Epub 2017 Jun 15.
6
Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives.高价碘(III)介导的脱羧Ritter 型胺化反应,生成α-叔胺衍生物。
J Org Chem. 2017 Nov 17;82(22):11711-11720. doi: 10.1021/acs.joc.7b01202. Epub 2017 Jun 27.
7
Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters.无金属催化、可见光促进的芳基 N-羟基邻苯二甲酰亚胺酯的脱羧硼化反应。
J Am Chem Soc. 2017 Jun 7;139(22):7440-7443. doi: 10.1021/jacs.7b03127. Epub 2017 May 24.
8
Decarboxylative borylation.脱羧硼化反应
Science. 2017 Jun 9;356(6342). doi: 10.1126/science.aam7355. Epub 2017 Apr 13.
9
Metal-Catalyzed Decarboxylative C-H Functionalization.金属催化脱羧 C-H 功能化。
Chem Rev. 2017 Jul 12;117(13):8864-8907. doi: 10.1021/acs.chemrev.6b00516. Epub 2017 Mar 7.
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J Org Chem. 2016 Aug 19;81(16):7250-5. doi: 10.1021/acs.joc.6b01360. Epub 2016 Jul 18.