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Birth of organocatalysis by N-heterocyclic carbenes N-heterocyclic carbenes 有机催化的诞生
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-23 DOI: 10.1038/s41929-024-01235-z
Sukriyo Chakraborty, Akkattu T. Biju
{"title":"Birth of organocatalysis by N-heterocyclic carbenes","authors":"Sukriyo Chakraborty, Akkattu T. Biju","doi":"10.1038/s41929-024-01235-z","DOIUrl":"10.1038/s41929-024-01235-z","url":null,"abstract":"Thiamine, a common enzymatic cofactor, catalyses the benzoin condensation. From 1943, a panoply of mechanistic proposals were invoked to explain the intriguing transformation until two seminal papers by Ronald Breslow about 15 years after the discovery of this reaction helped resolve the mechanistic conundrum and heralded the birth of NHC-organocatalysis.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 10","pages":"1060-1062"},"PeriodicalIF":42.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487875","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photocatalytic generation of alkyl carbanions from aryl alkenes 光催化生成芳基烯烃的烷基碳离子
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-23 DOI: 10.1038/s41929-024-01237-x
Milena L. Czyz, Tyra H. Horngren, Andrew J. Kondopoulos, Liam J. Franov, José A. Forni, Le Nhan Pham, Michelle L. Coote, Anastasios Polyzos
{"title":"Photocatalytic generation of alkyl carbanions from aryl alkenes","authors":"Milena L. Czyz, Tyra H. Horngren, Andrew J. Kondopoulos, Liam J. Franov, José A. Forni, Le Nhan Pham, Michelle L. Coote, Anastasios Polyzos","doi":"10.1038/s41929-024-01237-x","DOIUrl":"10.1038/s41929-024-01237-x","url":null,"abstract":"Organometallic reagents are routinely used as fundamental building blocks in organic chemistry to rapidly diversify molecular fragments via carbanion intermediates. However, the catalytic generation of carbanion equivalents, particularly from sp3-hybridized alkyl scaffolds, remains an underdeveloped goal in chemical synthesis. Here we disclose an approach for the generation of alkyl carbanions via single-electron reduction of aryl alkenes, enabled by multi-photon photoredox catalysis. We demonstrate that photocatalytically induced alkyl carbanions engage in intermolecular C–C bond-forming reactions with carbonyl electrophiles. Central to this method is the controlled formation of an alkene distonic radical anion intermediate that undergoes nucleophilic addition, followed by a kinetically favoured reductive polar crossover to produce a second carbanion available for further diversification. The versatility of this protocol was illustrated by the development of four distinct intermolecular C–C bond-forming reactions with aromatic alkenes (hydroalkoxylation, hydroamidation, aminoalkylation and carboxyaminoalkylation) to generate a range of valuable and complex scaffolds. Catalytic conversion of alkenes into carbanion equivalents usually requires stoichiometric reductants. Now an alternative strategy to access alkyl carbanion equivalents from abundant alkenes with the help of visible light photocatalysis is reported and used in four distinct C–C bond-forming reactions.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 12","pages":"1316-1329"},"PeriodicalIF":42.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.nature.com/articles/s41929-024-01237-x.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Anchored epoxidation 锚定环氧化
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-23 DOI: 10.1038/s41929-024-01247-9
Benjamin Martindale
{"title":"Anchored epoxidation","authors":"Benjamin Martindale","doi":"10.1038/s41929-024-01247-9","DOIUrl":"10.1038/s41929-024-01247-9","url":null,"abstract":"","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 10","pages":"1054-1054"},"PeriodicalIF":42.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Deconvoluting the cation effect on carbon monoxide electroreduction 解除阳离子对一氧化碳电还原的影响
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-23 DOI: 10.1038/s41929-024-01228-y
{"title":"Deconvoluting the cation effect on carbon monoxide electroreduction","authors":"","doi":"10.1038/s41929-024-01228-y","DOIUrl":"10.1038/s41929-024-01228-y","url":null,"abstract":"The performance of the electrochemical CO2 and CO reduction reactions is affected by the presence of alkali metal cations in the electrolyte, but the mechanism remains under debate. Now, experimental determination of the energetics and kinetic barriers of key elementary steps in the electrochemical CO reduction reaction on Cu enables deconvolution of the cation effect.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 10","pages":"1063-1064"},"PeriodicalIF":42.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487874","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoredox-catalysed amidyl radical insertion to bicyclo[1.1.0]butanes 光氧化催化酰胺基插入双环[1.1.0]丁烷
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-22 DOI: 10.1038/s41929-024-01239-9
Chetan C. Chintawar, Ranjini Laskar, Debanjan Rana, Felix Schäfer, Nele Van Wyngaerden, Subhabrata Dutta, Constantin G. Daniliuc, Frank Glorius
{"title":"Photoredox-catalysed amidyl radical insertion to bicyclo[1.1.0]butanes","authors":"Chetan C. Chintawar, Ranjini Laskar, Debanjan Rana, Felix Schäfer, Nele Van Wyngaerden, Subhabrata Dutta, Constantin G. Daniliuc, Frank Glorius","doi":"10.1038/s41929-024-01239-9","DOIUrl":"10.1038/s41929-024-01239-9","url":null,"abstract":"Replacing planar aromatic rings in drug molecules with C(sp3)-rich isosteric mimetics, such as bicyclo[n.1.1]alkanes, can significantly alter their physicochemical and pharmacokinetic properties, often leading to higher clinical success rates. However, unlike a benzene ring, the structurally rigid C(sp3)-rich isosteric mimetics of heteroaromatic rings are rare. Heterobicyclo[n.1.1]alkanes are promising in this regard, but the lack of modular synthetic methods has currently hindered their exploration. We envisioned that the strategic and selective insertion of different heteroatomic units to bicyclo[1.1.0]butanes could offer a highly modular platform to access diverse heterobicyclo[n.1.1]alkanes. Herein we report a photoredox-catalysed highly regioselective and chemoselective insertion of amidyl radicals to bicyclo[1.1.0]butanes, providing direct access to 2-oxa-4-azabicyclo[3.1.1]hept-3-enes. The exit vector analysis shows a geometric resemblance of these C(sp3)-rich heterobicyclic motifs with pyridine and pyrimidine derivatives, suggesting their potential as isosteric mimetics of such medicinally important heterocycles. Additionally, various downstream transformations demonstrate their utility as versatile building blocks in synthetic chemistry. Heteroatom-substituted C(sp3)-rich polycyclic hydrocarbon rings, isosteric to heterocyclic rings, are not common due to the challenging synthesis. Now a photoredox-catalysed strategy to insert amidyl radicals into bicyclo[1.1.0]butanes is presented, providing direct access to 2-oxa-4-azabicyclo[3.1.1]hept-3-enes.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 11","pages":"1232-1242"},"PeriodicalIF":42.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.nature.com/articles/s41929-024-01239-9.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The iron-catalysed Suzuki coupling of aryl chlorides 铁催化的芳基氯化物铃木偶联反应
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-17 DOI: 10.1038/s41929-024-01234-0
Benjamin J. S. Rowsell, Harry M. O’Brien, Gayathri Athavan, Patrick R. Daley-Dee, Johannes Krieger, Emma Richards, Karl Heaton, Ian J. S. Fairlamb, Robin B. Bedford
{"title":"The iron-catalysed Suzuki coupling of aryl chlorides","authors":"Benjamin J. S. Rowsell, Harry M. O’Brien, Gayathri Athavan, Patrick R. Daley-Dee, Johannes Krieger, Emma Richards, Karl Heaton, Ian J. S. Fairlamb, Robin B. Bedford","doi":"10.1038/s41929-024-01234-0","DOIUrl":"10.1038/s41929-024-01234-0","url":null,"abstract":"The very widely exploited Suzuki biaryl coupling reaction typically requires catalysts based on palladium, but there is an increasing desire to replace this metal with a more sustainable, less expensive alternative, with catalysts based on iron being a particularly attractive target. Here we show that a simple iron-based catalyst with an N-heterocyclic carbene ligand can be used to excellent effect in the Suzuki biaryl coupling of aryl chloride substrates with aryl boronic esters activated by an organolithium reagent. Mechanistic studies suggest the possible involvement of Fe(I) as the lowest oxidation state on the catalytic manifold and show that the challenging step is not activation of the aryl chloride substrate, but rather the transmetallation step. These findings are likely to lead to a renaissance of iron-catalysed carbon–carbon bond-forming transformations with soft nucleophilic coupling partners. The replacement of palladium with other metal catalysts in C–C bond-forming reactions is attractive in terms of costs and sustainability. Now an iron-based catalyst is successfully employed in the Suzuki cross-coupling of aryl chlorides with aryl boronic esters activated with tert-butyl lithium.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 11","pages":"1186-1198"},"PeriodicalIF":42.8,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.nature.com/articles/s41929-024-01234-0.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142440846","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Atom-by-atom design of Cu/ZrOx clusters on MgO for CO2 hydrogenation using liquid-phase atomic layer deposition 利用液相原子层沉积技术在氧化镁上逐个原子设计用于二氧化碳加氢的铜/氧化锆团簇
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-14 DOI: 10.1038/s41929-024-01236-y
Seongmin Jin, Choah Kwon, Aram Bugaev, Bartu Karakurt, Yu-Cheng Lin, Louisa Savereide, Liping Zhong, Victor Boureau, Olga Safonova, Sangtae Kim, Jeremy S. Luterbacher
{"title":"Atom-by-atom design of Cu/ZrOx clusters on MgO for CO2 hydrogenation using liquid-phase atomic layer deposition","authors":"Seongmin Jin, Choah Kwon, Aram Bugaev, Bartu Karakurt, Yu-Cheng Lin, Louisa Savereide, Liping Zhong, Victor Boureau, Olga Safonova, Sangtae Kim, Jeremy S. Luterbacher","doi":"10.1038/s41929-024-01236-y","DOIUrl":"10.1038/s41929-024-01236-y","url":null,"abstract":"The difficulty of synthesizing uniform atomically precise active sites limits our ability to engineer increasingly more active heterogeneous catalysts for the hydrogenation of CO2 to methanol. Here we design Cu/ZrOx clusters on MgO with near atomic precision for CO2 hydrogenation using a liquid-phase atomic layer deposition method. The controlled cluster structure modulates the binding strength of CO2 and moderately stabilizes monodentate formate—an essential reaction intermediate for methanol production. We achieved a methanol selectivity of 100 and 76.7% at 200 and 250 °C, respectively and a methanol productivity that was one to two orders of magnitude higher than when the same catalysts were prepared by impregnation. Ab initio computations show that Cu/ZrOx clusters can tune the oxidation of Zr, which controls the stability of reaction intermediates on the catalyst. Our approach demonstrates the potential of precise atomic control of catalytic clusters to improve catalytic productivity. Achieving atomic control during the synthesis of heterogeneous catalysts remains challenging. Here the authors tackle this challenge by applying a liquid-phase atomic layer deposition approach to the synthesis of Cu/ZrOx clusters on MgO as efficient catalysts for CO2 hydrogenation to methanol.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 11","pages":"1199-1212"},"PeriodicalIF":42.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142430570","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iron-catalysed cooperative redox mechanism for the simultaneous conversion of nitrous oxide and nitric oxide 铁催化的同时转化一氧化二氮和一氧化氮的合作氧化还原机制
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-10 DOI: 10.1038/s41929-024-01231-3
Filippo Buttignol, Jörg W. A. Fischer, Adam H. Clark, Martin Elsener, Alberto Garbujo, Pierdomenico Biasi, Izabela Czekaj, Maarten Nachtegaal, Gunnar Jeschke, Oliver Kröcher, Davide Ferri
{"title":"Iron-catalysed cooperative redox mechanism for the simultaneous conversion of nitrous oxide and nitric oxide","authors":"Filippo Buttignol, Jörg W. A. Fischer, Adam H. Clark, Martin Elsener, Alberto Garbujo, Pierdomenico Biasi, Izabela Czekaj, Maarten Nachtegaal, Gunnar Jeschke, Oliver Kröcher, Davide Ferri","doi":"10.1038/s41929-024-01231-3","DOIUrl":"10.1038/s41929-024-01231-3","url":null,"abstract":"Iron-exchanged zeolites are often deployed industrially to remediate nitric oxide (NO) and nitrous oxide (N2O) emissions. The nature of the active site and the reaction mechanism involved in the simultaneous removal of NO and N2O remain largely unknown, primarily because of the heterogeneity of Fe species. Here we combined catalytic experiments with transient operando X-ray absorption spectroscopy, electron paramagnetic resonance and diffuse reflectance infrared Fourier transform spectroscopy to disentangle the nature of Fe species and elementary reaction steps. We identified spectroscopically the square-planar Fe2+ sites in the β-cationic position responsible for N2O activation and the related redox cycle. These sites communicate with tetrahedrally coordinated Fe2+ sites in the adjacent γ-cationic position, accounting for adsorption and redox-mediated oxidation of NO. The availability of NH3 adsorbed on neighbouring Brønsted acid sites regulates the overall reaction rate of this dual-site mechanism by intercepting the NO oxidation sequence. The cooperation between these redox processes ensures enhanced conversion of both NO and N2O. Fe-exchanged zeolite catalysts are known for their ability to remediate NOx and N2O emissions, but their reactivity in mixed streams of NO and N2O remains unclear. Now a suite of operando spectroscopies reveals the active Fe species involved in the process and their synergistic effect during the simultaneous conversion of these pollutants.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 12","pages":"1305-1315"},"PeriodicalIF":42.8,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398246","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organocatalytic asymmetric α-C–H functionalization of alkyl amines 烷基胺的有机催化不对称 α-C-H 功能化
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-03 DOI: 10.1038/s41929-024-01230-4
Tianran Deng, Xiang-Lei Han, Yang Yu, Cheng Cheng, Xiangyuan Liu, Yuhong Gao, Keqiang Wu, Zhenghua Li, Jisheng Luo, Li Deng
{"title":"Organocatalytic asymmetric α-C–H functionalization of alkyl amines","authors":"Tianran Deng, Xiang-Lei Han, Yang Yu, Cheng Cheng, Xiangyuan Liu, Yuhong Gao, Keqiang Wu, Zhenghua Li, Jisheng Luo, Li Deng","doi":"10.1038/s41929-024-01230-4","DOIUrl":"10.1038/s41929-024-01230-4","url":null,"abstract":"Catalytic enantioselective α-C–H functionalization of widely available achiral alkyl amines could provide an ideal synthetic approach towards chiral amines. However, the inert nature of the α-C–H of alkyl amines renders their activation as carbanionic nucleophiles for catalytic asymmetric reactions an important yet unmet challenge. Here we describe how N-arylidene-protected alkyl amines could be activated as carbanions for asymmetric conjugate addition and the Mannich reaction. These results represent an intriguing and generally useful approach to the synthesis of chiral α,α-dialkyl amines. More importantly, they highlight the enormous potential of N-arylidene-protected amines as readily available and widely applicable synthons for the asymmetric synthesis of chiral amines. The catalytic activation of alkyl amines as α-nitrogen carbanions is challenging. Now the activation of N-arylidene-protected alkyl amines as carbanions by chiral ammonium organocatalysis for asymmetric conjugate addition and the Mannich reaction is reported, affording chiral α,α-dialkyl amines.","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 10","pages":"1076-1085"},"PeriodicalIF":42.8,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142368994","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Author Correction: Localized thermal levering events drive spontaneous kinetic oscillations during CO oxidation on Rh/Al2O3 作者更正:局部热杠杆事件驱动 Rh/Al2O3 上 CO 氧化过程中的自发动力学振荡
IF 42.8 1区 化学
Nature Catalysis Pub Date : 2024-10-03 DOI: 10.1038/s41929-024-01240-2
Donato Decarolis, Monik Panchal, Matthew Quesne, Khaled Mohammed, Shaojun Xu, Mark Isaacs, Adam H. Clark, Luke L. Keenan, Takuo Wakisaka, Kohei Kusada, Hiroshi Kitagawa, C. Richard A. Catlow, Emma K. Gibson, Alexandre Goguet, Peter P. Wells
{"title":"Author Correction: Localized thermal levering events drive spontaneous kinetic oscillations during CO oxidation on Rh/Al2O3","authors":"Donato Decarolis, Monik Panchal, Matthew Quesne, Khaled Mohammed, Shaojun Xu, Mark Isaacs, Adam H. Clark, Luke L. Keenan, Takuo Wakisaka, Kohei Kusada, Hiroshi Kitagawa, C. Richard A. Catlow, Emma K. Gibson, Alexandre Goguet, Peter P. Wells","doi":"10.1038/s41929-024-01240-2","DOIUrl":"10.1038/s41929-024-01240-2","url":null,"abstract":"","PeriodicalId":18845,"journal":{"name":"Nature Catalysis","volume":"7 11","pages":"1243-1243"},"PeriodicalIF":42.8,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.nature.com/articles/s41929-024-01240-2.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142368993","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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