可见光诱导钯催化芳基三氟甲磺酸酯生成芳基自由基
Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.
作者信息
Ratushnyy Maxim, Kvasovs Nikita, Sarkar Sumon, Gevorgyan Vladimir
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL, 60607-7061, USA.
Department of Chemistry and Biochemistry, University of Texas at Dallas, 800 West Campbell, BSB13, Richardson, TX, 75080, USA.
出版信息
Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10316-10320. doi: 10.1002/anie.201915962. Epub 2020 Apr 6.
Abstract
A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.
摘要
报道了一种温和的可见光诱导的钯催化酰胺分子内C-H芳基化反应。该方法通过C(sp)-O键的断裂来进行，生成杂化芳基钯自由基中间体。随后的1,5-氢原子迁移、分子内环化和再芳构化步骤生成了有价值的羟吲哚和异吲哚啉-1-酮结构单元。值得注意的是，该方法能够得到含有易烯醇化官能团的产物，而这些官能团与传统钯催化条件不相容。
相似文献
1
Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.可见光诱导钯催化芳基三氟甲磺酸酯生成芳基自由基
Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10316-10320. doi: 10.1002/anie.201915962. Epub 2020 Apr 6.
2
Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.钯催化的远程非活化 C(sp )-H 位点原子转移自由基环化反应：杂化乙烯基钯自由基中间体的氢原子转移。
Angew Chem Int Ed Engl. 2018 Mar 1;57(10):2712-2715. doi: 10.1002/anie.201712775. Epub 2018 Feb 6.
3
Visible Light Mediated Photoredox Catalytic Arylation Reactions.可见光介导的光氧化还原催化芳基化反应。
Acc Chem Res. 2016 Aug 16;49(8):1566-77. doi: 10.1021/acs.accounts.6b00229. Epub 2016 Aug 2.
4
Palladium-catalyzed desulfitative arylation by C-O bond cleavage of aryl triflates with sodium arylsulfinates.钯催化的通过芳基三氟甲磺酸酯与芳基亚磺酸钠的 C-O 键断裂的脱硫芳基化反应。
J Org Chem. 2012 Nov 16;77(22):10468-72. doi: 10.1021/jo302005s. Epub 2012 Nov 7.
5
Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp)-H Cross-Coupling.镍/光氧化还原 C(sp)-H 交叉偶联中氯光消除的合成和机理意义。
Acc Chem Res. 2021 Feb 16;54(4):988-1000. doi: 10.1021/acs.accounts.0c00694. Epub 2021 Jan 29.
6
Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.钯和镍的二氟膦配合物催化酮与芳基三氟甲磺酸酯的对映选择性α-芳基化反应。
J Am Chem Soc. 2008 Jan 9;130(1):195-200. doi: 10.1021/ja074453g. Epub 2007 Dec 13.
7
From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction.从烯烃的α-芳基化到与醛的酰化：Heck 反应区域控制的历程。
Acc Chem Res. 2011 Aug 16;44(8):614-26. doi: 10.1021/ar200053d. Epub 2011 May 25.
8
Iodine(III) Reagents in Radical Chemistry.碘(III)试剂在自由基化学中的应用。
Acc Chem Res. 2017 Jul 18;50(7):1712-1724. doi: 10.1021/acs.accounts.7b00148. Epub 2017 Jun 21.
9
Visible-Light-Induced Palladium-Catalyzed Construction of Polyarylfuran Skeletons via Cascade Aryl Radical Cyclization and C(sp)-P(V) Bond Cleavage.可见光诱导钯催化的多芳基呋喃骨架的构建：通过级联芳基自由基环化和 C(sp)-P(V) 键断裂。
Org Lett. 2023 Jun 30;25(25):4720-4724. doi: 10.1021/acs.orglett.3c01680. Epub 2023 Jun 20.
10
Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent.可见光照耀下镍和有机染料共催化的芳基卤化物和三氟甲磺酸酯与溴代乙烯以及二乙氧基乙酸的甲酰化反应，其中二乙氧基乙酸作为甲酰化试剂。
Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1500-1505. doi: 10.1002/anie.201610108. Epub 2017 Jan 9.
引用本文的文献
1
Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer.通过光驱动单电子转移将有机铋化合物作为芳基自由基前体
ACS Catal. 2024 Feb 16;14(4):2664-2670. doi: 10.1021/acscatal.3c05598. Epub 2024 Feb 6.
2
Illuminating Palladium Catalysis.钯催化的阐释
Acc Chem Res. 2025 Mar 18;58(6):861-876. doi: 10.1021/acs.accounts.4c00815. Epub 2025 Feb 26.
3
Recent Advances in Visible Light Induced Palladium Catalysis.可见光诱导钯催化的最新进展
Angew Chem Int Ed Engl. 2024 Feb 26;63(9):e202311972. doi: 10.1002/anie.202311972. Epub 2023 Nov 27.
4
Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C-O bond cleavage.通过选择性C-O键裂解实现芳基三氟甲磺酸酯的有机介导电化学氟磺酰化反应。
Nat Commun. 2023 Oct 31;14(1):6933. doi: 10.1038/s41467-023-42699-0.
5
Advances in Selected Heterocyclization Methods.特定杂环化方法的进展
Synlett. 2023 Aug;34(13):1554-1562. doi: 10.1055/s-0042-1751429. Epub 2023 Mar 10.
6
Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes.钯-氢键增强的激发态氢给体性质实现了烯烃的首例头-尾氢烷化反应。
J Am Chem Soc. 2023 Jun 7;145(22):12224-12232. doi: 10.1021/jacs.3c02410. Epub 2023 May 24.
7
Aryl-to-alkyl radical relay Heck reaction of amides with vinyl arenes.酰胺与乙烯基芳烃的芳基到烷基的自由基接力Heck反应。
Chem Sci. 2023 Feb 27;14(13):3580-3586. doi: 10.1039/d2sc06852d. eCollection 2023 Mar 29.
8
Excited-State Palladium-Catalyzed α-Selective -Ketonylation.激发态钯催化的α选择性酮基化反应
CCS Chem. 2023 Jan;5(1):106-116. doi: 10.31635/ccschem.022.202202282. Epub 2022 Oct 10.
9
Catalytic Asymmetric Synthesis of Tröger's Base Analogues with Nitrogen Stereocenter.含氮立体中心的特罗格碱类似物的催化不对称合成。
ACS Cent Sci. 2023 Jan 4;9(1):64-71. doi: 10.1021/acscentsci.2c01121. eCollection 2023 Jan 25.
10
General and Selective Metal-Free Radical -C-H Borylation of Aliphatic Amines.脂肪族胺的通用和选择性无金属自由基-C-H硼化反应
Chem. 2022 Nov;8(11):3096-3108. doi: 10.1016/j.chempr.2022.07.022. Epub 2022 Aug 22.
本文引用的文献
1
C-H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes.电生成高价碘物种与钌配合物双催化实现的C-H氧化反应
Angew Chem Int Ed Engl. 2020 Feb 17;59(8):3184-3189. doi: 10.1002/anie.201914226. Epub 2020 Jan 9.
2
Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization.钯催化烯烃双官能团化合成全碳季碳中心。
Angew Chem Int Ed Engl. 2020 Feb 3;59(6):2375-2379. doi: 10.1002/anie.201911012. Epub 2020 Jan 9.
3
Palladium-catalyzed cascade reactions of alkene-tethered carbamoyl chlorides with N-tosyl hydrazones: synthesis of alkene-functionalized oxindoles.钯催化的烯丙基酰胺氯与 N-对甲苯磺酰腙的级联反应：烯基官能化的吲哚酮的合成。
Org Biomol Chem. 2019 Sep 28;17(36):8358-8363. doi: 10.1039/c9ob01672d. Epub 2019 Aug 29.
4
Visible-light-induced deboronative alkylarylation of acrylamides with organoboronic acids.可见光诱导的丙烯酰胺与有机硼酸的脱硼烷基芳基化反应。
Org Biomol Chem. 2019 Jul 21;17(27):6612-6619. doi: 10.1039/c9ob01023h. Epub 2019 Jun 24.
5
Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.使用接力Heck策略实现钯催化的烯内酰胺对映选择性烯基化反应。
Chemistry. 2019 Aug 14;25(46):10823-10827. doi: 10.1002/chem.201902813. Epub 2019 Jul 26.
6
Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts.钯催化的可见光驱动的芳基和烯基三氟甲磺酸酯的羧基化反应：使用光氧化还原催化剂
Org Lett. 2019 Jun 21;21(12):4486-4489. doi: 10.1021/acs.orglett.9b01340. Epub 2019 Jun 10.
7
Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams.多组分反应（MCRs）：合成苯并稠合γ-内酰胺的有效途径。
Beilstein J Org Chem. 2019 May 8;15:1065-1085. doi: 10.3762/bjoc.15.104. eCollection 2019.
8
Catalytic β C-H amination an imidate radical relay.催化β C-H胺化：一种亚胺酸酯自由基接力反应。
Chem Sci. 2019 Jan 17;10(9):2693-2699. doi: 10.1039/c8sc05685d. eCollection 2019 Mar 7.
9
δ C-H (hetero)arylation Cu-catalyzed radical relay.δ C-H（杂）芳基化 铜催化的自由基接力反应
Chem Sci. 2018 Nov 9;10(4):1207-1211. doi: 10.1039/c8sc04366c. eCollection 2019 Jan 28.
10
Catalysis with Palladium Complexes Photoexcited by Visible Light.可见光激发的钯配合物催化作用。
Angew Chem Int Ed Engl. 2019 Aug 19;58(34):11586-11598. doi: 10.1002/anie.201813523. Epub 2019 May 24.
Zotero 插件