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脂肪醇的仿生催化远程去饱和反应

Biomimetic Catalytic Remote Desaturation of Aliphatic Alcohols.

作者信息

Zuo Kaiming, Zhu Jing, Akhtar Faral, Dam Phong, Azofra Luis Miguel, El-Sepelgy Osama

机构信息

Leibniz Institute for Catalysis e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany.

Instituto de Estudios Ambientales y Recursos Naturales (i-UNAT), Universidad de Las Palmas de Gran Canaria (ULPGC), Campus de Tafira, 35017 Las Palmas de Gran Canaria, Spain.

出版信息

Org Lett. 2025 Jan 10;27(1):30-35. doi: 10.1021/acs.orglett.4c03623. Epub 2024 Dec 23.

DOI:10.1021/acs.orglett.4c03623
PMID:39714251
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11731365/
Abstract

Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis of valuable cyclic and acyclic allylic and homoallylic alcohols from readily available saturated aliphatic alcohols. Remarkably, this method obviates the need for external oxidants, noble metal catalysts, and phosphine ligands.

摘要

在此,我们展示了光诱导钴肟催化的脂肪醇选择性远程去饱和反应。这种转化在室温下能高效进行,可从容易获得的饱和脂肪醇合成有价值的环状和非环状烯丙基醇及高烯丙基醇。值得注意的是,该方法无需外部氧化剂、贵金属催化剂和膦配体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/a7b28d494ff3/ol4c03623_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/5cfbdea2c764/ol4c03623_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/8286623048b9/ol4c03623_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/6461f6352d04/ol4c03623_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/6abb8bb81305/ol4c03623_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/255a59779e53/ol4c03623_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/a7b28d494ff3/ol4c03623_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/5cfbdea2c764/ol4c03623_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/8286623048b9/ol4c03623_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/6461f6352d04/ol4c03623_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/6abb8bb81305/ol4c03623_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/255a59779e53/ol4c03623_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bd2/11731365/a7b28d494ff3/ol4c03623_0003.jpg

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本文引用的文献

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Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis.有机合成中的仿生光激发钴肟催化
Angew Chem Int Ed Engl. 2024 Aug 12;63(33):e202405775. doi: 10.1002/anie.202405775. Epub 2024 Jul 15.
2
Organic thermally activated delayed fluorescence material with strained benzoguanidine donor.具有张力苯并胍供体的有机热活化延迟荧光材料。
Beilstein J Org Chem. 2023 Sep 7;19:1289-1298. doi: 10.3762/bjoc.19.95. eCollection 2023.
3
Photoexcited cobalt catalysed -selective alkyl Heck reaction.光激发钴催化的 - 选择性烷基Heck反应。 (注:原文中“ -selective”这里的“-”不太明确其准确含义,可能是有遗漏或错误表述,但按照要求完整翻译了。)
Chem Commun (Camb). 2023 Mar 28;59(26):3862-3865. doi: 10.1039/d2cc06967a.
4
Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light.可见光下钴催化的通过自由基转移实现的化学选择性脱氢反应
Chem Sci. 2022 Jun 15;13(26):7947-7954. doi: 10.1039/d2sc02291e. eCollection 2022 Jul 6.
5
Photo-Induced Ruthenium-Catalyzed Double Remote C(sp )-H / C(sp )-H Functionalizations by Radical Relay.光诱导钌催化的自由基接力远程双C(sp³)-H / C(sp³)-H官能团化反应
Angew Chem Int Ed Engl. 2022 Aug 8;61(32):e202205562. doi: 10.1002/anie.202205562. Epub 2022 Jun 10.
6
Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis.受生物启发的醇的光氧化还原质子耦合电子转移和钴双催化去饱和作用。
Nat Commun. 2022 Feb 10;13(1):809. doi: 10.1038/s41467-022-28441-2.
7
Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis.金属光氧化还原:光氧化还原与过渡金属催化的融合
Chem Rev. 2022 Jan 26;122(2):1485-1542. doi: 10.1021/acs.chemrev.1c00383. Epub 2021 Nov 18.
8
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Nat Commun. 2021 Nov 4;12(1):6404. doi: 10.1038/s41467-021-26670-5.
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Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis.有机光氧化还原/钴双催化实现脂肪族化合物的位点选择性无受体脱氢反应
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