Suppr超能文献

氢化铜催化的烯烃和炔烃的氢胺化反应

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.

作者信息

Pirnot Michael T, Wang Yi-Ming, Buchwald Stephen L

机构信息

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA).

出版信息

Angew Chem Int Ed Engl. 2016 Jan 4;55(1):48-57. doi: 10.1002/anie.201507594. Epub 2015 Dec 10.

Abstract

Over the past few years, CuH-catalyzed hydroamination has been discovered and developed as a robust and conceptually novel approach for the synthesis of enantioenriched secondary and tertiary amines. The success in this area of research was made possible through the large body of precedent in copper(I) hydride catalysis and the well-explored use of hydroxylamine esters as electrophilic amine sources in related copper-catalyzed processes. This Minireview details the background, advances, and mechanistic investigations in CuH-catalyzed hydroamination.

摘要

在过去几年中,氢化亚铜催化的氢胺化反应已被发现并发展成为一种用于合成对映体富集仲胺和叔胺的稳健且概念新颖的方法。该研究领域的成功得益于氢化亚铜催化方面的大量先例以及在相关铜催化过程中作为亲电胺源的羟胺酯的广泛应用。本综述详细介绍了氢化亚铜催化氢胺化反应的背景、进展和机理研究。

相似文献

1
Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):48-57. doi: 10.1002/anie.201507594. Epub 2015 Dec 10.
2
Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination.
J Am Chem Soc. 2015 Aug 5;137(30):9716-21. doi: 10.1021/jacs.5b05446. Epub 2015 Jul 21.
3
A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination.
J Am Chem Soc. 2018 Nov 21;140(46):15976-15984. doi: 10.1021/jacs.8b10564. Epub 2018 Nov 8.
4
Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.
J Am Chem Soc. 2013 Oct 23;135(42):15746-9. doi: 10.1021/ja4092819. Epub 2013 Oct 15.
5
A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.
Angew Chem Int Ed Engl. 2018 Jul 9;57(28):8714-8718. doi: 10.1002/anie.201803026. Epub 2018 Jun 12.
6
CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.
Acc Chem Res. 2020 Jun 16;53(6):1229-1243. doi: 10.1021/acs.accounts.0c00164. Epub 2020 May 13.
8
Hydroamination: direct addition of amines to alkenes and alkynes.
Chem Rev. 2008 Sep;108(9):3795-892. doi: 10.1021/cr0306788. Epub 2008 Aug 26.
9
Enantioselective CuH-catalyzed anti-Markovnikov hydroamination of 1,1-disubstituted alkenes.
J Am Chem Soc. 2014 Nov 12;136(45):15913-6. doi: 10.1021/ja509786v. Epub 2014 Oct 29.
10
Intramolecular hydroamination of aminoalkenes catalyzed by a cationic zirconium complex.
Org Lett. 2011 Sep 16;13(18):4758-61. doi: 10.1021/ol201731m. Epub 2011 Aug 12.

引用本文的文献

1
Remote Migratory Reductive Arylation of Unactivated Alkenes Enabled by Electrochemical Nickel Catalysis.
ChemSusChem. 2025 Mar 15;18(6):e202402196. doi: 10.1002/cssc.202402196. Epub 2024 Nov 19.
3
Metal-Hydride C-C Cross-Coupling of Alkenes Through a Double Outer-Sphere Mechanism.
J Org Chem. 2024 Nov 15;89(22):16106-16113. doi: 10.1021/acs.joc.4c00260. Epub 2024 Jun 26.
4
Photocatalytic Anti-Markovnikov Hydroamination of Alkenes with Primary Heteroaryl Amines.
J Am Chem Soc. 2023 Oct 11;145(40):21738-21744. doi: 10.1021/jacs.3c08428. Epub 2023 Oct 3.
5
Locating Interstitial Hydrides in MH@Cu (M = Cu, Ag) Clusters by Single-Crystal X-ray Diffraction.
ACS Omega. 2023 Aug 15;8(34):31541-31547. doi: 10.1021/acsomega.3c04758. eCollection 2023 Aug 29.
6
Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View.
Chem Rev. 2023 Aug 9;123(15):9139-9203. doi: 10.1021/acs.chemrev.2c00482. Epub 2023 Jul 5.
7
Rhodium-/Iridium-Catalyzed Hydroamination for the Synthesis of 1,2-, 1,3-, or 1,4-Diamines.
ACS Catal. 2022 Jul 15;12(14):8331-8340. doi: 10.1021/acscatal.2c01835. Epub 2022 Jun 28.
8
-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters.
Chem Sci. 2022 Nov 24;13(48):14387-14394. doi: 10.1039/d2sc06003e. eCollection 2022 Dec 14.
10

本文引用的文献

1
Hydroformylation of Internal Olefins to Linear Aldehydes with Novel Rhodium Catalysts.
Angew Chem Int Ed Engl. 1999 Feb 1;38(3):336-338. doi: 10.1002/(SICI)1521-3773(19990201)38:3<336::AID-ANIE336>3.0.CO;2-P.
2
Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination.
J Am Chem Soc. 2015 Aug 5;137(30):9716-21. doi: 10.1021/jacs.5b05446. Epub 2015 Jul 21.
4
Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter.
Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7847-51. doi: 10.1002/anie.201501762. Epub 2015 May 26.
5
Ligand-controlled regiodivergent Cu-catalyzed aminoboration of unactivated terminal alkenes.
J Am Chem Soc. 2015 May 27;137(20):6460-3. doi: 10.1021/jacs.5b02775. Epub 2015 May 15.
6
Late transition metal-catalyzed hydroamination and hydroamidation.
Chem Rev. 2015 Apr 8;115(7):2596-697. doi: 10.1021/cr300389u. Epub 2015 Feb 27.
7
Copper-catalysed selective hydroamination reactions of alkynes.
Nat Chem. 2015 Jan;7(1):38-44. doi: 10.1038/nchem.2131. Epub 2014 Dec 15.
8
Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes.
Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1638-41. doi: 10.1002/anie.201410326. Epub 2014 Dec 4.
9
Copper-catalyzed stereoselective aminoboration of bicyclic alkenes.
Angew Chem Int Ed Engl. 2015 Jan 7;54(2):613-7. doi: 10.1002/anie.201409104. Epub 2014 Nov 17.
10
Enantioselective CuH-catalyzed anti-Markovnikov hydroamination of 1,1-disubstituted alkenes.
J Am Chem Soc. 2014 Nov 12;136(45):15913-6. doi: 10.1021/ja509786v. Epub 2014 Oct 29.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验