利用借氢法实现钌催化仲醇的胺化反应
Ruthenium-Catalyzed Amination of Secondary Alcohols using Borrowing Hydrogen Methodology.
作者信息
Marichev Kostiantyn O, Takacs James M
机构信息
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, United States.
出版信息
ACS Catal. 2016 Apr 1;6(4):2205-2210. doi: 10.1021/acscatal.6b00175. Epub 2016 Feb 23.
Abstract
A new ruthenium complex catalyzes the amination of primary and secondary alcohols and the regioselective mono- and sequential diamination of diols via the borrowing hydrogen pathway. Several variations on new intra- and intermolecular cyclizations of aminoalcohols, diols and diamines lead to heterocyclic ring systems.
摘要
一种新型钌配合物通过借氢途径催化伯醇和仲醇的胺化反应以及二醇的区域选择性单胺化和连续二胺化反应。氨基醇、二醇和二胺的新型分子内和分子间环化反应的多种变体可生成杂环体系。
相似文献
1
Ruthenium-Catalyzed Amination of Secondary Alcohols using Borrowing Hydrogen Methodology.利用借氢法实现钌催化仲醇的胺化反应
ACS Catal. 2016 Apr 1;6(4):2205-2210. doi: 10.1021/acscatal.6b00175. Epub 2016 Feb 23.
2
Ruthenium pincer-catalyzed synthesis of substituted γ-butyrolactones using hydrogen autotransfer methodology.钌钳形催化剂通过氢自转移方法催化合成取代γ-丁内酯。
Chem Commun (Camb). 2015 Aug 25;51(66):13082-5. doi: 10.1039/c5cc01708d.
3
(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols.对映选择性氢转移：钌催化脲和二醇合成恶唑烷-2-酮。
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7826-30. doi: 10.1002/anie.201600698. Epub 2016 Apr 13.
4
Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen.通过借氢实现二醇构建手性邻二胺的催化非对映和对映选择性合成。
Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18599-18604. doi: 10.1002/anie.202101517. Epub 2021 Jul 16.
5
Ruthenium-catalyzed tertiary amine formation from nitroarenes and alcohols.钌催化硝基芳烃和醇生成叔胺。
Org Lett. 2010 Nov 5;12(21):4888-91. doi: 10.1021/ol1020527.
6
Cobalt-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer.钴催化仲醇与伯醇通过借氢/氢自转移进行的烷基化反应
Chemistry. 2017 Sep 7;23(50):12110-12113. doi: 10.1002/chem.201701211. Epub 2017 May 19.
7
Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy.无膦钌配合物催化通过借氢策略合成单烷基化或二烷基化酰肼
J Org Chem. 2021 May 7;86(9):6813-6825. doi: 10.1021/acs.joc.1c00654. Epub 2021 Apr 20.
8
Alkynyl Borrowing: Silver-Catalyzed Amination of Secondary Propargylic Alcohols via C(sp)-C(sp) Bond Cleavage.炔基借代：通过 C(sp)-C(sp) 键断裂的银催化仲丙炔醇的氨化反应。
J Org Chem. 2022 Apr 15;87(8):5395-5403. doi: 10.1021/acs.joc.2c00297. Epub 2022 Apr 6.
9
An efficient N-heterocyclic carbene-ruthenium complex: application towards the synthesis of polyesters and polyamides.一种高效的氮杂环卡宾-钌配合物：在聚酯和聚酰胺合成中的应用。
Macromol Rapid Commun. 2015 Mar;36(6):547-52. doi: 10.1002/marc.201400699. Epub 2015 Feb 4.
10
Ruthenium-catalyzed selective monoamination of vicinal diols.钌催化邻二醇的选择性单胺化反应。
ChemSusChem. 2009;2(6):551-7. doi: 10.1002/cssc.200900034.
引用本文的文献
1
Pd/C-Catalyzed Tandem Synthesis of β-Amino Alcohol Using Epoxide through Transfer Hydrogenation of Nitroarene with Methanol.钯/碳催化下通过硝基芳烃与甲醇的转移氢化反应，利用环氧化物串联合成β-氨基醇
ACS Omega. 2025 Jan 21;10(4):3494-3499. doi: 10.1021/acsomega.4c07580. eCollection 2025 Feb 4.
2
Bifunctional Imine Reductase Cascades for the Synthesis of Saturated -Heterocycles.用于合成饱和杂环的双功能亚胺还原酶级联反应
ACS Catal. 2024 Sep 19;14(19):14703-14710. doi: 10.1021/acscatal.4c03832. eCollection 2024 Oct 4.
3
Synthetic Protocols, Structural Activity Relationship, and Biological Activity of Piperazine and its Derivatives.哌嗪及其衍生物的合成方案、结构活性关系和生物活性。
Med Chem. 2024;20(8):753-780. doi: 10.2174/0115734064304396240415110015.
4
Regioselective Rearrangement of Nitrogen- and Carbon-Centered Radical Intermediates in the Hofmann-Löffler-Freytag Reaction.霍夫曼-勒夫勒-弗雷泰格反应中氮中心和碳中心自由基中间体的区域选择性重排
J Phys Chem A. 2024 Apr 4;128(13):2574-2583. doi: 10.1021/acs.jpca.3c07892. Epub 2024 Mar 22.
5
Effect of Re promoter on the structure and catalytic performance of Ni-Re/AlO catalysts for the reductive amination of monoethanolamine.Re 助剂对 Ni-Re/Al₂O₃ 催化剂用于单乙醇胺还原胺化反应的结构及催化性能的影响
RSC Adv. 2018 Feb 20;8(15):8152-8163. doi: 10.1039/c7ra12891f. eCollection 2018 Feb 19.
6
Control of Absolute Stereochemistry in Transition-Metal-Catalysed Hydrogen-Borrowing Reactions.过渡金属催化的氢借反应中绝对立体化学的控制。
Chemistry. 2020 Oct 9;26(57):12912-12926. doi: 10.1002/chem.202001253. Epub 2020 Sep 11.
7
Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or HS with alcohols.纳米层状硫化钴钼（Co-Mo-S）催化硫醇或HS与醇的借氢C-S键形成反应。
Chem Sci. 2019 Feb 4;10(10):3130-3142. doi: 10.1039/c8sc05782f. eCollection 2019 Mar 14.
8
Continuous -alkylation reactions of amino alcohols using γ-AlO and supercritical CO: unexpected formation of cyclic ureas and urethanes by reaction with CO.使用γ-氧化铝和超临界二氧化碳对氨基醇进行连续烷基化反应：与二氧化碳反应意外生成环状脲和聚氨酯。
Beilstein J Org Chem. 2017 Feb 21;13:329-337. doi: 10.3762/bjoc.13.36. eCollection 2017.
9
Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides.苄基三氯乙酰胺的重排反应。
J Org Chem. 2017 Apr 7;82(7):3982-3989. doi: 10.1021/acs.joc.7b00245. Epub 2017 Mar 27.
10
Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes.锰手性钳状配合物催化的胺与醇的高效和选择性 N-烷基化反应。
Nat Commun. 2016 Oct 6;7:12641. doi: 10.1038/ncomms12641.
本文引用的文献
1
Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols.钴催化的醇对芳胺的烷基化反应。
Angew Chem Int Ed Engl. 2015 Dec 7;54(50):15046-50. doi: 10.1002/anie.201507955. Epub 2015 Oct 16.
2
A Sustainable Multicomponent Pyrimidine Synthesis.一种可持续的多组分嘧啶合成方法。
J Am Chem Soc. 2015 Oct 14;137(40):12804-7. doi: 10.1021/jacs.5b09510. Epub 2015 Oct 1.
3
Iron-catalyzed amination of alcohols assisted by Lewis acid.路易斯酸辅助的铁催化醇的胺化反应
Chem Commun (Camb). 2015 Jul 28;51(59):11907-10. doi: 10.1039/c5cc03399c.
4
Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines.醇的动态动力学非对映选择性胺化：从四种异构体的混合物到非对映和对映纯的α-支链胺。
J Am Chem Soc. 2015 Apr 22;137(15):4944-7. doi: 10.1021/jacs.5b02212. Epub 2015 Apr 8.
5
Chemoenzymatic asymmetric synthesis of 1,4-benzoxazine derivatives: application in the synthesis of a levofloxacin precursor.1,4-苯并恶嗪衍生物的化学酶不对称合成：在左氧氟沙星前体合成中的应用
J Org Chem. 2015 Apr 17;80(8):3815-24. doi: 10.1021/acs.joc.5b00056. Epub 2015 Mar 27.
6
Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation.通过过渡金属催化脱氢反应，用 N-亲核试剂替代醇。
Chem Soc Rev. 2015 Apr 21;44(8):2305-29. doi: 10.1039/c4cs00496e.
7
New iridium catalysts for the selective alkylation of amines by alcohols under mild conditions and for the synthesis of quinolines by acceptor-less dehydrogenative condensation.用于在温和条件下通过醇对胺进行选择性烷基化以及通过无受体脱氢缩合合成喹啉的新型铱催化剂。
Chemistry. 2014 Oct 6;20(41):13279-85. doi: 10.1002/chem.201402952. Epub 2014 Sep 3.
8
Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology.在温和条件下使用借氢方法通过钌催化胺与醇的N-烷基化反应。
J Org Chem. 2014 Aug 15;79(16):7553-63. doi: 10.1021/jo501273t. Epub 2014 Jul 24.
9
Stereoselective synthesis of polysubstituted piperazines and oxopiperazines. Useful building blocks in medicinal chemistry.立体选择性合成多取代哌嗪和氧代哌嗪。在药物化学中有重要的应用价值。
Curr Top Med Chem. 2014;14(10):1308-16. doi: 10.2174/1568026614666140423114013.
10
The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation.通过铱催化的无受体脱氢烷基化反应，由芳香族二胺和醇类合成苯并咪唑和喹喔啉。
Chemistry. 2014 May 5;20(19):5569-72. doi: 10.1002/chem.201400400. Epub 2014 Apr 7.
Zotero 插件