通过氢化锆和氨化反应一锅法反马氏加成的未活化烯烃的氢胺化反应。
One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.
机构信息
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA.
出版信息
J Org Chem. 2013 Sep 6;78(17):8909-14. doi: 10.1021/jo401498w. Epub 2013 Aug 27.
Abstract
A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.
摘要
本文报道了一种烯烃的一锅反马氏加成氨氢化反应。在多种官能团存在的条件下，可从非活化烯烃合成伯胺和仲胺。通过锆氢化反应，然后与氮亲电试剂进行胺化反应，可得到高立体选择性的反马氏加成产物。大多数产物无需柱层析即可高产率分离得到。
相似文献
1
One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.通过氢化锆和氨化反应一锅法反马氏加成的未活化烯烃的氢胺化反应。
J Org Chem. 2013 Sep 6;78(17):8909-14. doi: 10.1021/jo401498w. Epub 2013 Aug 27.
2
Intramolecular hydroamination of aminoalkenes catalyzed by a cationic zirconium complex.氨烯丙基化反应的分子内催化作用由阳离子锆络合物。
Org Lett. 2011 Sep 16;13(18):4758-61. doi: 10.1021/ol201731m. Epub 2011 Aug 12.
3
Catalytic hydroamination of unactivated olefins using a Co catalyst for complex molecule synthesis.使用 Co 催化剂催化非活化烯烃的氢胺化反应，用于复杂分子的合成。
J Am Chem Soc. 2014 Oct 1;136(39):13534-7. doi: 10.1021/ja507295u. Epub 2014 Sep 22.
4
Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines.未活化烯烃与伯烷基胺的反 Markovnikov 氢胺化反应。
J Am Chem Soc. 2019 Oct 23;141(42):16590-16594. doi: 10.1021/jacs.9b08746. Epub 2019 Oct 14.
5
Catalytic enantioselective allylic amination of unactivated terminal olefins via an ene reaction/[2,3]-rearrangement.通过烯反应/[2,3]-重排实现非活化末端烯烃的催化对映选择性烯丙基胺化。
J Am Chem Soc. 2012 Nov 14;134(45):18495-8. doi: 10.1021/ja307851b. Epub 2012 Oct 29.
6
Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.对映选择性和区域选择性的铜氢催化烯烃的氢胺化反应。
J Am Chem Soc. 2013 Oct 23;135(42):15746-9. doi: 10.1021/ja4092819. Epub 2013 Oct 15.
7
Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.由末端烯烃合成叔烷基胺：烷基硼烷的铜催化胺化反应。
J Am Chem Soc. 2012 Apr 18;134(15):6571-4. doi: 10.1021/ja3023829. Epub 2012 Apr 10.
8
Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.氢化铜催化的烯烃和炔烃的氢胺化反应
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):48-57. doi: 10.1002/anie.201507594. Epub 2015 Dec 10.
9
Hydroamination: direct addition of amines to alkenes and alkynes.氢胺化反应：胺类直接加成到烯烃和炔烃上。
Chem Rev. 2008 Sep;108(9):3795-892. doi: 10.1021/cr0306788. Epub 2008 Aug 26.
10
Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.配体控制的铱催化非活化烯烃的区域选择性氧胺化反应。
J Am Chem Soc. 2019 Jul 31;141(30):11864-11869. doi: 10.1021/jacs.9b06366. Epub 2019 Jul 16.
引用本文的文献
1
A catalytic process enables efficient and programmable access to precisely altered indole alkaloid scaffolds.一种催化过程能够实现高效、可编程地获得精确修饰的吲哚生物碱支架。
Nat Chem. 2024 Jun;16(6):1003-1014. doi: 10.1038/s41557-024-01455-7. Epub 2024 Feb 19.
2
Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View.烯烃和炔烃的反马氏规则分子间氢胺化反应：机理视角
Chem Rev. 2023 Aug 9;123(15):9139-9203. doi: 10.1021/acs.chemrev.2c00482. Epub 2023 Jul 5.
3
Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono-Mannich Reaction.通过会聚 Petasis 硼诺-曼尼希反应的全合成 Strempeliopidine 和非天然对映异构体。
J Am Chem Soc. 2023 Apr 5;145(13):7278-7287. doi: 10.1021/jacs.2c13146. Epub 2023 Mar 23.
4
Lithium Enolate with a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine.锂烯醇与锂-炔键相互作用在对映选择性构建季碳中心中的应用：（+）-戈米辛的简洁合成。
Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202209987. doi: 10.1002/anie.202209987. Epub 2022 Oct 17.
5
Total Synthesis and Functional Evaluation of IORs, Sulfonolipid-based Inhibitors of Cell Differentiation in Salpingoeca rosetta.IORs 的全合成及功能评价，罗氏沼虾输卵管中分化抑制性磺基脂类化合物
Angew Chem Int Ed Engl. 2022 Oct 10;61(41):e202209105. doi: 10.1002/anie.202209105. Epub 2022 Sep 5.
6
Site-selective amination and/or nitrilation metal-free C(sp)-C(sp) cleavage of benzylic and allylic alcohols.苄醇和烯丙醇的位点选择性胺化和/或腈化：无金属的C(sp)-C(sp)键裂解
Chem Sci. 2022 Apr 5;13(17):4821-4827. doi: 10.1039/d2sc00758d. eCollection 2022 May 4.
7
Enantioselective hydroamination of unactivated terminal alkenes.未活化末端烯烃的对映选择性氢胺化反应。
Chem. 2022 Feb 10;8(2):532-542. doi: 10.1016/j.chempr.2021.12.005. Epub 2022 Jan 11.
8
Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes.三溴化硼作为使HBr对环丙烷进行反马氏加成反应的试剂。
Chem Sci. 2020 Aug 4;11(35):9426-9433. doi: 10.1039/d0sc02567d.
9
Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.手性催化非环季碳中心的合成：全取代非环烯醇碳酸酯的钯催化脱羧烯丙基烷基化反应。
J Am Chem Soc. 2018 Aug 15;140(32):10109-10112. doi: 10.1021/jacs.8b05560. Epub 2018 Aug 2.
10
Persulfate Reaction in a Hair-Bleaching Formula: Unveiling the Unconventional Reactivity of 1,13-Diamino-4,7,10-Trioxatridecane.头发漂白配方中的过硫酸盐反应：揭示1,13 - 二氨基 - 4,7,10 - 三氧杂十三烷的非常规反应活性
ChemistryOpen. 2018 Mar 25;7(5):319-322. doi: 10.1002/open.201800013. eCollection 2018 May.
本文引用的文献
1
Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.芳基硼酸的难以捉摸的无金属伯胺化：通过密度泛函理论的合成研究和机理。
J Am Chem Soc. 2012 Nov 7;134(44):18253-6. doi: 10.1021/ja309637r. Epub 2012 Oct 25.
2
Direct stereospecific amination of alkyl and aryl pinacol boronates.烷基和芳基频哪醇硼酸酯的直接对映选择性胺化。
J Am Chem Soc. 2012 Oct 10;134(40):16449-51. doi: 10.1021/ja305448w. Epub 2012 Sep 24.
3
Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.由末端烯烃合成叔烷基胺：烷基硼烷的铜催化胺化反应。
J Am Chem Soc. 2012 Apr 18;134(15):6571-4. doi: 10.1021/ja3023829. Epub 2012 Apr 10.
4
Synthesis of hindered anilines: copper-catalyzed electrophilic amination of aryl boronic esters.受阻苯胺的合成：芳基硼酸酯的铜催化亲电胺化反应。
Angew Chem Int Ed Engl. 2012 Apr 16;51(16):3953-6. doi: 10.1002/anie.201200480. Epub 2012 Mar 7.
5
Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines.铜催化芳基硼酸酯与N,N-二烷基羟胺的胺化反应。
Angew Chem Int Ed Engl. 2012 Apr 10;51(15):3642-5. doi: 10.1002/anie.201108773. Epub 2012 Mar 1.
6
2-Allylphenyl glycosides as glycosyl donors for sugar coupling.2-烯丙基苯基糖苷作为糖基供体用于糖偶联。
Carbohydr Res. 2012 May 1;352:197-201. doi: 10.1016/j.carres.2012.01.022. Epub 2012 Feb 7.
7
Neuroprotective effects of N-alkyl-1,2,4-oxadiazolidine-3,5-diones and their corresponding synthetic intermediates N-alkylhydroxylamines and N-1-alkyl-3-carbonyl-1-hydroxyureas against in vitro cerebral ischemia.N- 烷基-1,2,4-恶二唑烷-3,5-二酮及其相应的合成中间体 N- 烷基羟胺和 N-1-烷基-3-羰基-1-羟基脲对体外脑缺血的神经保护作用。
ChemMedChem. 2010 Jan;5(1):79-85. doi: 10.1002/cmdc.200900418.
8
Iridium-catalyzed regio- and enantioselective N-allylation of indoles.铱催化吲哚的区域和对映选择性N-烯丙基化反应。
Angew Chem Int Ed Engl. 2009;48(42):7841-4. doi: 10.1002/anie.200904338.
9
Selective C-H activation alpha to primary amines. Bridging metallaaziridines for catalytic, intramolecular alpha-alkylation.伯胺α位的选择性C-H活化。用于催化分子内α-烷基化的桥连金属氮丙啶。
J Am Chem Soc. 2009 Feb 18;131(6):2116-8. doi: 10.1021/ja808862w.
10
Hydroamination: direct addition of amines to alkenes and alkynes.氢胺化反应：胺类直接加成到烯烃和炔烃上。
Chem Rev. 2008 Sep;108(9):3795-892. doi: 10.1021/cr0306788. Epub 2008 Aug 26.
Zotero 插件