以α'-羟基烯酮作为酰化试剂的催化酰胺形成反应。
Catalytic amide formation with alpha'-hydroxyenones as acylating reagents.
作者信息
Chiang Pei-Chen, Kim Yoonjoo, Bode Jeffrey W
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, USA.
出版信息
Chem Commun (Camb). 2009 Aug 14(30):4566-8. doi: 10.1039/b909360e. Epub 2009 Jul 6.
Abstract
Alpha'-hydroxyenones undergo clean, catalytic amidations with amines promoted by the combination of an N-heterocyclic carbene and 1,2,4-triazole.
摘要
α'-羟基烯酮在氮杂环卡宾和1,2,4-三唑的组合促进下，能与胺进行清洁的催化酰胺化反应。
相似文献
1
Catalytic amide formation with alpha'-hydroxyenones as acylating reagents.
Chem Commun (Camb). 2009 Aug 14(30):4566-8. doi: 10.1039/b909360e. Epub 2009 Jul 6.
2
N-heterocyclic carbene-catalyzed redox amidations of alpha-functionalized aldehydes with amines.
J Am Chem Soc. 2007 Nov 14;129(45):13798-9. doi: 10.1021/ja0768136. Epub 2007 Oct 23.
3
Concerted amidation of activated esters: reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer.
J Am Chem Soc. 2014 Aug 20;136(33):11783-91. doi: 10.1021/ja505784w. Epub 2014 Aug 8.
4
Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.
J Am Chem Soc. 2012 May 16;134(19):8094-7. doi: 10.1021/ja3030164. Epub 2012 May 2.
5
Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with -Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines.
Molecules. 2018 Sep 20;23(10):2413. doi: 10.3390/molecules23102413.
6
Oxonitriles: a grignard addition-acylation route to enamides.
Org Lett. 2006 Oct 12;8(21):4903-6. doi: 10.1021/ol0619765.
7
Catalytic acylation of amines with aldehydes or aldoximes.
Org Lett. 2010 Nov 19;12(22):5096-9. doi: 10.1021/ol101978h. Epub 2010 Oct 14.
8
NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.
J Am Chem Soc. 2014 Mar 5;136(9):3362-5. doi: 10.1021/ja500373s. Epub 2014 Feb 20.
9
N-Acyltriazinedione; a Novel Acylating Reagent Synthesized from a Triazinone-Type Condensing Reagent.
Chem Pharm Bull (Tokyo). 2021;69(5):498-502. doi: 10.1248/cpb.c20-00952.
10
N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.
J Am Chem Soc. 2009 Dec 23;131(50):18028-9. doi: 10.1021/ja9094044.
引用本文的文献
1
Kinetics and Mechanism of Azole n-π*-Catalyzed Amine Acylation.
J Am Chem Soc. 2023 Aug 16;145(32):18126-18140. doi: 10.1021/jacs.3c06258. Epub 2023 Aug 1.
2
Bio-inspired NHC-organocatalyzed Stetter reaction in aqueous conditions.
RSC Adv. 2020 Nov 9;10(67):40709-40718. doi: 10.1039/d0ra08326g.
3
Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes.
Chem Sci. 2016 Jan 1;7(1):713-718. doi: 10.1039/c5sc03510d. Epub 2015 Oct 22.
4
Direct amidation of non-activated phenylacetic acid and benzylamine derivatives catalysed by NiCl.
R Soc Open Sci. 2018 Feb 21;5(2):171870. doi: 10.1098/rsos.171870. eCollection 2018 Feb.
5
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.
Chem Rev. 2015 Sep 9;115(17):9307-87. doi: 10.1021/acs.chemrev.5b00060. Epub 2015 May 20.
6
Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.
Chem Sci. 2013 Apr;4(4):1674-1679. doi: 10.1039/C3SC00089C.
7
Asymmetric -Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.
Aldrichimica Acta. 2011;44(1):3-11.
8
Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.
Org Lett. 2014 Sep 19;16(18):4714-7. doi: 10.1021/ol502089v. Epub 2014 Sep 8.
9
The effect of the -mesityl group in NHC-catalyzed reactions.
Chem Sci. 2012 Jan 1;3(1):192-197. doi: 10.1039/C1SC00397F.
10
Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.
Adv Synth Catal. 2012 Jun 18;354(9):1617-1639. doi: 10.1002/adsc.201200031. Epub 2012 Apr 19.
本文引用的文献
1
Simple one-pot conversion of aldehydes and ketones to enals.
Org Lett. 2009 May 21;11(10):2117-9. doi: 10.1021/ol9005757.
2
Acyl transfer catalysis with 1,2,4-triazole anion.
Org Lett. 2009 Apr 2;11(7):1499-502. doi: 10.1021/ol900098q.
3
Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines.
Angew Chem Int Ed Engl. 2009;48(3):559-63. doi: 10.1002/anie.200804757.
4
Chemoselective ligation and modification strategies for peptides and proteins.
Angew Chem Int Ed Engl. 2008;47(52):10030-74. doi: 10.1002/anie.200801313.
5
Amide synthesis from alcohols and amines by the extrusion of dihydrogen.
J Am Chem Soc. 2008 Dec 31;130(52):17672-3. doi: 10.1021/ja808129p.
6
Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature.
Angew Chem Int Ed Engl. 2008;47(15):2876-9. doi: 10.1002/anie.200705468.
7
Organocatalysis by N-heterocyclic carbenes.
Chem Rev. 2007 Dec;107(12):5606-55. doi: 10.1021/cr068372z. Epub 2007 Oct 23.
8
N-heterocyclic carbene-catalyzed redox amidations of alpha-functionalized aldehydes with amines.
J Am Chem Soc. 2007 Nov 14;129(45):13798-9. doi: 10.1021/ja0768136. Epub 2007 Oct 23.
9
Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.
J Am Chem Soc. 2007 Nov 14;129(45):13796-7. doi: 10.1021/ja0764052. Epub 2007 Oct 11.
10
Direct synthesis of amides from alcohols and amines with liberation of H2.
Science. 2007 Aug 10;317(5839):790-2. doi: 10.1126/science.1145295.
Zotero 插件