酮基 ABNO/NOx 共催化醛的有氧氧化为羧酸，并通过连续不对称加氢甲酰化/氧化获得 α-手性羧酸。
KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.
机构信息
Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
出版信息
Org Lett. 2016 Aug 5;18(15):3590-3. doi: 10.1021/acs.orglett.6b01598. Epub 2016 Jul 13.
Abstract
A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.
摘要
已开发出一种使用有机氮氧自由基和 NOx 共催化剂将醛氧化为羧酸的方法。酮基 ABNO（9-氮杂双环[3.3.1]壬烷-3-酮 N-氧自由基）和 NaNO2 分别被鉴定为最佳氮氧自由基和 NOx 来源。反应条件温和，可使烯烃/有氧醛的连续不对称氢甲酰化/氧化转化为α-手性羧酸，而不会外消旋化。该氧化方法的范围、实用性和局限性还通过一系列带有不同官能团的手性醛进行了评估。
相似文献
1
KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.酮基 ABNO/NOx 共催化醛的有氧氧化为羧酸，并通过连续不对称加氢甲酰化/氧化获得 α-手性羧酸。
Org Lett. 2016 Aug 5;18(15):3590-3. doi: 10.1021/acs.orglett.6b01598. Epub 2016 Jul 13.
2
An insight into the mechanism of the aerobic oxidation of aldehydes catalyzed by N-heterocyclic carbenes.氮杂环卡宾催化醛的有氧氧化反应机理的研究进展。
Chem Commun (Camb). 2014 Feb 25;50(16):2008-11. doi: 10.1039/c3cc48929a.
3
TMSCN/DBU-mediated facile redox transformation of α,β-unsaturated aldehydes to carboxylic acid derivatives.TMSCN/DBU 介导的α,β-不饱和醛到羧酸衍生物的简便氧化还原转化。
Org Lett. 2014 Feb 7;16(3):727-9. doi: 10.1021/ol403415z. Epub 2014 Jan 21.
4
CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.CuH 催化的 α,β-不饱和羧酸的不对称还原反应生成β-手性醛。
J Am Chem Soc. 2018 Jan 17;140(2):606-609. doi: 10.1021/jacs.7b12260. Epub 2018 Jan 4.
5
Functionalisation of aldehydes via aerobic hydroacylation of azodicarboxylates 'on' water.通过在水中对偶氮二羧酸酯进行需氧氢酰化作用来实现醛的功能化。
Chem Commun (Camb). 2011 Mar 21;47(11):3269-71. doi: 10.1039/c0cc04520a. Epub 2011 Feb 1.
6
Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes.系统的生物催化氢转移级联开发方法：在手性α-取代α,β-不饱和醛合成α-取代羧酸中的应用。
Org Biomol Chem. 2015 Jan 7;13(1):223-33. doi: 10.1039/c4ob02282c.
7
A supramolecular catalyst for the decarboxylative hydroformylation of alpha,beta-unsaturated carboxylic acids.一种用于α,β-不饱和羧酸脱羧氢甲酰化反应的超分子催化剂。
Angew Chem Int Ed Engl. 2008;47(21):3946-9. doi: 10.1002/anie.200800956.
8
gem-Dibromomethylarenes: a convenient substitute for noncommercial aldehydes in the knoevenagel-doebner reaction for the synthesis of alpha,beta-unsaturated carboxylic acids.偕二溴甲基芳烃：一种在克诺文纳格尔-多布纳反应中用于合成α,β-不饱和羧酸的非商业醛的便捷替代物。
J Org Chem. 2007 Dec 7;72(25):9854-6. doi: 10.1021/jo701888m. Epub 2007 Nov 14.
9
Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.手性铜氢催化的利用不饱和羧酸作为醛替代物的对映选择性氢酰化反应。
J Am Chem Soc. 2017 Jun 21;139(24):8126-8129. doi: 10.1021/jacs.7b04937. Epub 2017 Jun 6.
10
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation.铁催化的α,β-不饱和羧酸的多米诺脱羧-氧化反应能够实现醛的 C-H 甲基化。
Chem Commun (Camb). 2021 Jun 15;57(48):5905-5908. doi: 10.1039/d1cc01536b.
引用本文的文献
1
A cobalt adduct of an N-hydroxy-piperidinium cation.一种N-羟基哌啶鎓阳离子的钴加合物。
J Coord Chem. 2022;75(11-14):1853-1864. doi: 10.1080/00958972.2022.2119557. Epub 2022 Sep 14.
2
The Al-Containing Silicates Modified with Organic Ligands and SnO Nanoparticles for Catalytic Baeyer-Villiger Oxidation and Aerobic Carboxylation of Carbonyl Compounds.用于催化羰基化合物的拜耳-维利格氧化反应和需氧羧化反应的有机配体修饰的含铝硅酸盐和SnO纳米颗粒
Nanomaterials (Basel). 2023 Jan 20;13(3):433. doi: 10.3390/nano13030433.
3
Au/Ag/Cu-Mixed Catalysts for the Eco-Friendly Oxidation of 5-Hydroxymethylfurfural and Related Compounds to Carboxylic Acids under Atmospheric Oxygen in Water.用于在水中大气氧气条件下将5-羟甲基糠醛及相关化合物绿色氧化为羧酸的金/银/铜混合催化剂
ACS Omega. 2020 Dec 9;6(3):2239-2247. doi: 10.1021/acsomega.0c05526. eCollection 2021 Jan 26.
4
Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.氨基氧自由基促进的亚稳电荷转移复合物介导的烯烃电化学双氮氧化反应
J Am Chem Soc. 2019 Feb 20;141(7):2825-2831. doi: 10.1021/jacs.8b13192. Epub 2019 Jan 28.
本文引用的文献
1
High-Potential Electrocatalytic O2 Reduction with Nitroxyl/NO x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis.高电势电催化氧气还原与亚硝酰基/NOx 介体：对燃料电池和需氧氧化催化的影响。
ACS Cent Sci. 2015 Aug 26;1(5):234-43. doi: 10.1021/acscentsci.5b00163. Epub 2015 Jul 15.
2
Silver(I) as a widely applicable, homogeneous catalyst for aerobic oxidation of aldehydes toward carboxylic acids in water-"silver mirror": From stoichiometric to catalytic.银（I）作为一种广泛适用的均相催化剂，用于在水中将醛有氧氧化为羧酸——“银镜”：从化学计量到催化。
Sci Adv. 2015 Mar 27;1(2):e1500020. doi: 10.1126/sciadv.1500020. eCollection 2015 Mar.
3
Electrocatalytic Alcohol Oxidation with TEMPO and Bicyclic Nitroxyl Derivatives: Driving Force Trumps Steric Effects.使用 TEMPO 和双环氮氧自由基衍生物的电催化醇氧化：驱动力胜过空间效应。
J Am Chem Soc. 2015 Nov 25;137(46):14751-7. doi: 10.1021/jacs.5b09672. Epub 2015 Nov 13.
4
Asymmetric hydroformylation of Z-enamides and enol esters with rhodium-bisdiazaphos catalysts.手性双氮杂菲铑配合物催化 Z-烯酰胺和烯醇酯的不对称氢甲酰化反应。
J Am Chem Soc. 2014 Oct 15;136(41):14583-8. doi: 10.1021/ja507701k. Epub 2014 Oct 2.
5
Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems.醇类和胺类与均相铜/TEMPO及相关催化剂体系的实用需氧氧化反应
Angew Chem Int Ed Engl. 2014 Aug 18;53(34):8824-38. doi: 10.1002/anie.201403110. Epub 2014 Jul 7.
6
Selective aerobic oxidation of alcohols to aldehydes, carboxylic acids, and imines catalyzed by a Ag-NHC complex.由银-氮杂环卡宾配合物催化的醇选择性有氧氧化生成醛、羧酸和亚胺。
Org Lett. 2014 Jul 3;16(13):3428-31. doi: 10.1021/ol501353q. Epub 2014 Jun 17.
7
Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems.铜/2,2,6,6-四甲基哌啶氮氧化物催化的需氧醇氧化反应：不同催化剂体系的机理评估
ACS Catal. 2013 Nov 1;3(11):2599-2605. doi: 10.1021/cs400689a.
8
Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds.高化学选择性的氨基酸醇有氧氧化为氨基酸羰基化合物。
Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3236-40. doi: 10.1002/anie.201309634. Epub 2014 Feb 19.
9
Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems.铜（I）/ABNO 催化有氧醇氧化：缓解 Cu/TEMPO 催化剂体系的空间和电子约束。
J Am Chem Soc. 2013 Oct 23;135(42):15742-5. doi: 10.1021/ja409241h. Epub 2013 Oct 15.
10
Conversion of biomass into chemicals over metal catalysts.通过金属催化剂将生物质转化为化学品。
Chem Rev. 2014 Feb 12;114(3):1827-70. doi: 10.1021/cr4002269. Epub 2013 Oct 1.
Zotero 插件