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用Ag(OCCFSOF)和O实现烯烃的1,2-氧化三氟甲基化反应:α-三氟甲基酮的合成

1,2-Oxidative Trifluoromethylation of Olefin with Ag(OCCFSOF) and O: Synthesis of α-Trifluoromethyl Ketones.

作者信息

Zhang Shengxue, Xiao Wangchuan, Wu Jingjing, Wu Fanhong, Huang Houjin, Ma Xiaoyu, Shi Yafei, Liu Chao

机构信息

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China.

Shanghai-Sanming Engineering Research Center of Green Fluoropharmaceutical Technology, 25 Jingdong Road, Sanming 365004, China.

出版信息

Molecules. 2024 Nov 27;29(23):5622. doi: 10.3390/molecules29235622.

DOI:10.3390/molecules29235622
PMID:39683781
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643604/
Abstract

A novel and efficient 1,2-oxidative trifluoromethylation of olefins employing Ag(OCCFSOF) as a trifluoromethyl source is described with O as the oxidant, which provides access to a variety of valuable α-trifluoromethyl-substituted ketones. The broad substrate scope, feasibility of large-scale operation, and derivatization reactions of α-trifluoromethyl ketones demonstrate the promising utility of this protocol.

摘要

描述了一种新颖且高效的烯烃1,2-氧化三氟甲基化反应,该反应使用Ag(OCCFSOF)作为三氟甲基源,以氧气作为氧化剂,可得到多种有价值的α-三氟甲基取代的酮。α-三氟甲基酮广泛的底物范围、大规模操作的可行性以及衍生化反应证明了该方法具有广阔的应用前景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/49741e44f05f/molecules-29-05622-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/306130a7f1a8/molecules-29-05622-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/dd85aad13647/molecules-29-05622-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/ac4055ee9222/molecules-29-05622-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/49741e44f05f/molecules-29-05622-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/306130a7f1a8/molecules-29-05622-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/dd85aad13647/molecules-29-05622-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/ac4055ee9222/molecules-29-05622-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69bb/11643604/49741e44f05f/molecules-29-05622-sch004.jpg

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本文引用的文献

1
Efficient Trifluoromethylation of Halogenated Hydrocarbons Using Novel [(bpy)Cu(OCCFSOF)] Reagent.使用新型[(bpy)Cu(OCCFSOF)]试剂实现卤代烃的高效三氟甲基化反应。
Molecules. 2024 Jun 14;29(12):2849. doi: 10.3390/molecules29122849.
2
Cooperative Photoredox and N-Heterocyclic Carbene Catalyzed Fluoroaroylation for the Synthesis of α-Trifluoromethyl-Substituted Ketones.协同光氧化还原与氮杂环卡宾催化的氟芳酰化反应合成α-三氟甲基取代酮
Angew Chem Int Ed Engl. 2023 Nov 27;62(48):e202310288. doi: 10.1002/anie.202310288. Epub 2023 Oct 27.
3
Pyridinium-Masked Enol as a Precursor for Constructing Alpha-Fluoromethyl Ketones.
吡啶鎓掩蔽的烯醇作为构建α-氟甲基酮的前体。
Org Lett. 2023 Aug 25;25(33):6211-6216. doi: 10.1021/acs.orglett.3c02419. Epub 2023 Aug 16.
4
Amine-Induced Selective C-C Bond Cleavage of 2,2,2-Trifluoroethyl Carbonyls for the Synthesis of Ureas and Amides.
J Org Chem. 2023 Jul 21;88(14):10137-10146. doi: 10.1021/acs.joc.3c00979. Epub 2023 Jul 12.
5
Exploiting the inductive effect of the trifluoromethyl group: regioselective gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes.利用三氟甲基的诱导效应:2,2,2-三氟乙基取代炔烃的区域选择性金催化水合反应
Chem Commun (Camb). 2023 Jul 20;59(59):9138-9141. doi: 10.1039/d3cc02034g.
6
Photocatalytic Alkyl Radical Addition Tandem Oxidation of Alkenyl Borates.光催化烷基自由基加成串联氧化烯基硼酸酯。
J Org Chem. 2023 Apr 7;88(7):4325-4333. doi: 10.1021/acs.joc.2c02923. Epub 2023 Mar 20.
7
Photoinduced Trifluoromethylation with CFBr as a Trifluoromethyl Source: Synthesis of α-CF-Substituted Ketones.以CFBr作为三氟甲基源的光诱导三氟甲基化反应:α-三氟甲基取代酮的合成
ACS Omega. 2022 Apr 12;7(16):14357-14362. doi: 10.1021/acsomega.2c01241. eCollection 2022 Apr 26.
8
Three-Component Reactions of α-CF Carbonyls, NaN, and Amines for the Synthesis of -1,2,3-Triazoles.用于合成 -1,2,3- 三唑的 α-CF 羰基、NaN 和胺的三组分反应。
J Org Chem. 2021 Dec 3;86(23):17197-17212. doi: 10.1021/acs.joc.1c02288. Epub 2021 Nov 1.
9
Pd-catalyzed defluorination/arylation of α-trifluoromethyl ketones via consecutive β-F elimination and C-F bond activation.钯催化的α-三氟甲基酮通过连续β-F消除和C-F键活化的脱氟/芳基化反应。
Chem Commun (Camb). 2018 Apr 26;54(35):4406-4409. doi: 10.1039/c8cc01568f.
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Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15432-15435. doi: 10.1002/anie.201709663. Epub 2017 Nov 2.