Felipe C. Demidoff , Paulo R. R. Costa , Guilherme S. Caleffi
Rearranged homoisoflavonoids constitute a unique group of natural products, renowned for their structural diversity and complexity. These compounds, derived from modifications in the 3-benzylchroman skeleton, are categorized into four subclasses: brazilin, caesalpin, protosappanin, and scillascillin homoisoflavonoids. This review examines the advancements in the total synthesis of these complex structures, aiming to highlight the challenges and opportunities encountered. A comparative analysis of the strategies employed thus far to synthesize these compounds provides a comprehensive understanding of the progress in this field.
{"title":"Advances in the synthesis of rearranged homoisoflavonoids","authors":"Felipe C. Demidoff , Paulo R. R. Costa , Guilherme S. Caleffi","doi":"10.1039/d4ob00627e","DOIUrl":"10.1039/d4ob00627e","url":null,"abstract":"<div><p>Rearranged homoisoflavonoids constitute a unique group of natural products, renowned for their structural diversity and complexity. These compounds, derived from modifications in the 3-benzylchroman skeleton, are categorized into four subclasses: brazilin, caesalpin, protosappanin, and scillascillin homoisoflavonoids. This review examines the advancements in the total synthesis of these complex structures, aiming to highlight the challenges and opportunities encountered. A comparative analysis of the strategies employed thus far to synthesize these compounds provides a comprehensive understanding of the progress in this field.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141178292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Phong D. Nguyen, Truong K. Chau, Mai Q. Le, Manh T. Nguyen, Anh T. Nguyen and Tung T. Nguyen
The synthesis of medicinally relevant N-aryl-substituted 2-aminobenzothiazoles often uses 2-aminothiophenol derivatives, which are not commercially abundant, as starting materials. Herein, we report a method for the annulation of C3-substituted nitroarenes and aryl isothiocyanates towards the synthesis of 2-aminobenzothiazoles. Reactions proceeded in the presence of cobalt ferrite nanoparticles as a catalyst, DABCO as a base, and DMF as a promoter. The cobalt ferrite nanoparticles could be recovered after each run and reused up to 3 times while the product yield was not diminished. Our method appears to be the first example of the direct use of substituted nitroarenes for yielding 2-aminobenzothiazoles.
{"title":"Cobalt ferrite nanoparticles for annulation of C3-substituted nitroarenes and aryl isothiocyanates†","authors":"Phong D. Nguyen, Truong K. Chau, Mai Q. Le, Manh T. Nguyen, Anh T. Nguyen and Tung T. Nguyen","doi":"10.1039/D4OB00789A","DOIUrl":"10.1039/D4OB00789A","url":null,"abstract":"<p >The synthesis of medicinally relevant <em>N</em>-aryl-substituted 2-aminobenzothiazoles often uses 2-aminothiophenol derivatives, which are not commercially abundant, as starting materials. Herein, we report a method for the annulation of C3-substituted nitroarenes and aryl isothiocyanates towards the synthesis of 2-aminobenzothiazoles. Reactions proceeded in the presence of cobalt ferrite nanoparticles as a catalyst, DABCO as a base, and DMF as a promoter. The cobalt ferrite nanoparticles could be recovered after each run and reused up to 3 times while the product yield was not diminished. Our method appears to be the first example of the direct use of substituted nitroarenes for yielding 2-aminobenzothiazoles.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141416727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Daniel A. McNaughton , Edward York , Tristan Rawling , Philip A. Gale
The N,N′-dimethylation of a diphenylsquaramide induces a conformational change in the orientation of the phenyl rings. This has been exploited to create a series of bis-urea, -thiourea and -squaramide anionophores. The compounds were shown to bind to Cl− using proton NMR titration techniques and to transport H+/Cl− through the lipid bilayers, whereas a non-methylated analogue displayed limited transport activity. Despite their potency in transport studies, the series had a negligible impact on cancer cell viability.
{"title":"N,N′-Dimethylsquaramide as a central scaffold for anionophore design†","authors":"Daniel A. McNaughton , Edward York , Tristan Rawling , Philip A. Gale","doi":"10.1039/d4ob00703d","DOIUrl":"10.1039/d4ob00703d","url":null,"abstract":"<div><p>The <em>N</em>,<em>N</em>′-dimethylation of a diphenylsquaramide induces a conformational change in the orientation of the phenyl rings. This has been exploited to create a series of bis-urea, -thiourea and -squaramide anionophores. The compounds were shown to bind to Cl<sup>−</sup> using proton NMR titration techniques and to transport H<sup>+</sup>/Cl<sup>−</sup> through the lipid bilayers, whereas a non-methylated analogue displayed limited transport activity. Despite their potency in transport studies, the series had a negligible impact on cancer cell viability.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141064506","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Linqing Wang , Jiaming Lv , Yongshuo Zhang , Dongxu Yang
Magnesium catalysts are widely used in catalytic asymmetric reactions, and a series of catalytic strategies have been developed in recent years. Herein, in this review, we have tried to summarize asymmetric magnesium catalysis for the synthesis of important chiral scaffolds. Several important optically active motifs that are present in classic chiral ligands or natural products synthesized by Mg(ii) catalytic methods are briefly discussed. Moreover, the representative mechanisms for different magnesium catalytic strategies, including in situ generated magnesium catalysts, are also shown in relation to synthetic routes for obtaining these important chiral scaffolds.
{"title":"Asymmetric magnesium catalysis for important chiral scaffold synthesis","authors":"Linqing Wang , Jiaming Lv , Yongshuo Zhang , Dongxu Yang","doi":"10.1039/d4ob00521j","DOIUrl":"10.1039/d4ob00521j","url":null,"abstract":"<div><p>Magnesium catalysts are widely used in catalytic asymmetric reactions, and a series of catalytic strategies have been developed in recent years. Herein, in this review, we have tried to summarize asymmetric magnesium catalysis for the synthesis of important chiral scaffolds. Several important optically active motifs that are present in classic chiral ligands or natural products synthesized by Mg(<span>ii</span>) catalytic methods are briefly discussed. Moreover, the representative mechanisms for different magnesium catalytic strategies, including <em>in situ</em> generated magnesium catalysts, are also shown in relation to synthetic routes for obtaining these important chiral scaffolds.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141160473","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bromonitroalkenes are useful molecules in synthetic organic chemistry. They are mainly prepared from nitroalkenes via bromination reactions. In this review, the application of bromonitroalkenes as partners in the reaction with a diversity of mono- and bi-functional molecules, including aldehydes and ketones, active methylene compounds, 1,2-dicarbonyls, enamines, enols, electron-rich arenes, amidines, azomethine ylides, azirines, diazo compounds, and many others, is reviewed. By using these substrates, various biologically active scaffolds, such as heterocycles, carbocycles, spirocycles, polycyclic systems, natural products, and other useful acyclic compounds, were prepared. In addition, due to their dielectrophilic character, electrophilic and nucleophilic character, and ability to participate in cycloaddition reactions, bromonitroalkenes were efficiently applied in asymmetric cascade/domino/tandem reactions catalyzed by chiral catalysts. In this manuscript, around 55 papers are summarized and discussed during the years 2000–2023.
{"title":"Bromonitroalkenes as efficient intermediates in organic synthesis","authors":"Azim Ziyaei Halimehjani , Hoonam Tahvildari","doi":"10.1039/d4ob00221k","DOIUrl":"10.1039/d4ob00221k","url":null,"abstract":"<div><p>Bromonitroalkenes are useful molecules in synthetic organic chemistry. They are mainly prepared from nitroalkenes <em>via</em> bromination reactions. In this review, the application of bromonitroalkenes as partners in the reaction with a diversity of mono- and bi-functional molecules, including aldehydes and ketones, active methylene compounds, 1,2-dicarbonyls, enamines, enols, electron-rich arenes, amidines, azomethine ylides, azirines, diazo compounds, and many others, is reviewed. By using these substrates, various biologically active scaffolds, such as heterocycles, carbocycles, spirocycles, polycyclic systems, natural products, and other useful acyclic compounds, were prepared. In addition, due to their dielectrophilic character, electrophilic and nucleophilic character, and ability to participate in cycloaddition reactions, bromonitroalkenes were efficiently applied in asymmetric cascade/domino/tandem reactions catalyzed by chiral catalysts. In this manuscript, around 55 papers are summarized and discussed during the years 2000–2023.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141178305","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this paper, two near-infrared BODIPY photosensitizers, Id-BDPI and Cz-BDPI, were obtained by modifying the indole and carbazole aromatic heterocycles in the core of BODIPY. The maximum absorption wavelengths of Id-BDPI and Cz-BDPI were 694 nm and 722 nm, and their singlet oxygen yields were 48% and 48.4%, respectively. In the simulated tumor cell photodynamic therapy, Id-BDPI and Cz-BDPI could effectively inhibit the growth of A549 tumor cells under near-infrared light. Meanwhile, the lysosomal co-localization coefficients of Id-BDPI and Cz-BDPI with A549 tumor cells were 0.94 and 0.89, respectively, showing high lysosomal targeting ability and biocompatibility. The two-photon absorption cross sections measured at 1050 nm by the Z-scanning method were 661.8 GM and 715.6 GM, respectively, and Cz-BDPI was further successfully applied to two-photon fluorescence imaging and two-photon excited singlet oxygen generation in zebrafish. The above results indicate that the introduction of aromatic heterocycles can effectively enhance the photodynamic efficacy of BODIPY photosensitizers, and the larger two-photon absorption cross section also brings potential for two-photon photodynamic therapy applications.
{"title":"Near-infrared BODIPY photosensitizers for two-photon excited singlet oxygen generation and tumor cell photodynamic therapy.","authors":"Ruibo Liu, Ying Qian","doi":"10.1039/d4ob00706a","DOIUrl":"https://doi.org/10.1039/d4ob00706a","url":null,"abstract":"<p><p>In this paper, two near-infrared BODIPY photosensitizers, Id-BDPI and Cz-BDPI, were obtained by modifying the indole and carbazole aromatic heterocycles in the core of BODIPY. The maximum absorption wavelengths of Id-BDPI and Cz-BDPI were 694 nm and 722 nm, and their singlet oxygen yields were 48% and 48.4%, respectively. In the simulated tumor cell photodynamic therapy, Id-BDPI and Cz-BDPI could effectively inhibit the growth of A549 tumor cells under near-infrared light. Meanwhile, the lysosomal co-localization coefficients of Id-BDPI and Cz-BDPI with A549 tumor cells were 0.94 and 0.89, respectively, showing high lysosomal targeting ability and biocompatibility. The two-photon absorption cross sections measured at 1050 nm by the <i>Z</i>-scanning method were 661.8 GM and 715.6 GM, respectively, and Cz-BDPI was further successfully applied to two-photon fluorescence imaging and two-photon excited singlet oxygen generation in zebrafish. The above results indicate that the introduction of aromatic heterocycles can effectively enhance the photodynamic efficacy of BODIPY photosensitizers, and the larger two-photon absorption cross section also brings potential for two-photon photodynamic therapy applications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141416728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Marija Paurević, Aleksandra Maršavelski, Siniša Ivanković, Ranko Stojković, Rosana Ribić
Muramyl dipeptide (MDP) is the smallest essential peptidoglycan substructure capable of promoting both innate and adaptive immune responses. Herein, we report on the design, synthesis, and in vivo study of the adjuvant properties of two novel MDP analogs containing an achiral adamantyl moiety attached to the desmuramyl dipeptide (DMP) pharmacophore and additionally modified by one mannosyl subunit (derivative 7) or two mannosyl subunits (derivative 11). Mannose substructures were introduced in order to assess how the degree of mannosylation affects the immune response and nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) binding affinity, compared to the reference compound ManAdDMP. Both mannosylated MDP analogs showed improved immunomodulating properties, while the di-mannosylated derivative 11 displayed the highest, statistically significant increase in anti-OVA IgG production. In this study, for the first time, the di-mannosylated DMP derivative was synthesized and immunologically evaluated. Derivative 11 stimulates a Th-2-polarized type of immune reaction, similar to the reference compound ManAdDMP and MDP. Molecular dynamics (MD) simulations demonstrate that 11 has a higher NOD2 binding affinity than 7, indicating that introducing the second mannose significantly contributes to the binding affinity. Mannose interacts with key amino acid residues from the LRR hydrophobic pocket of the NOD2 receptor and loop 2.
{"title":"Di-mannosylation enhances the adjuvant properties of adamantane-containing desmuramyl peptides <i>in vivo</i>.","authors":"Marija Paurević, Aleksandra Maršavelski, Siniša Ivanković, Ranko Stojković, Rosana Ribić","doi":"10.1039/d4ob00592a","DOIUrl":"https://doi.org/10.1039/d4ob00592a","url":null,"abstract":"<p><p>Muramyl dipeptide (MDP) is the smallest essential peptidoglycan substructure capable of promoting both innate and adaptive immune responses. Herein, we report on the design, synthesis, and <i>in vivo</i> study of the adjuvant properties of two novel MDP analogs containing an achiral adamantyl moiety attached to the desmuramyl dipeptide (DMP) pharmacophore and additionally modified by one mannosyl subunit (derivative 7) or two mannosyl subunits (derivative 11). Mannose substructures were introduced in order to assess how the degree of mannosylation affects the immune response and nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) binding affinity, compared to the reference compound ManAdDMP. Both mannosylated MDP analogs showed improved immunomodulating properties, while the di-mannosylated derivative 11 displayed the highest, statistically significant increase in anti-OVA IgG production. In this study, for the first time, the di-mannosylated DMP derivative was synthesized and immunologically evaluated. Derivative 11 stimulates a Th-2-polarized type of immune reaction, similar to the reference compound ManAdDMP and MDP. Molecular dynamics (MD) simulations demonstrate that 11 has a higher NOD2 binding affinity than 7, indicating that introducing the second mannose significantly contributes to the binding affinity. Mannose interacts with key amino acid residues from the LRR hydrophobic pocket of the NOD2 receptor and loop 2.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141329745","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
David Calderón-Rangel, Ángel Rentería-Gómez, Alicia E. Cruz-Jiménez, Manuel A. Rentería Gómez, J. Oscar C. Jiménez-Halla and Rocío Gámez-Montaño
A series of linked-type 1,5-disubstituted tetrazoles (1,5-DS-Ts) were synthesised via an isocyanide-based multicomponent reaction (IMCR) and used as synthetic platforms to access bound-type polyheterocycles containing an epoxyisoindol-1(6H)-one scaffold under green conditions. This rapid sonochemical synthetic strategy includes a double domino process using an orthogonal heterocyclic input in the Ugi-azide (UA) reaction. DFT calculations and NBO analysis were performed to understand the pseudopericyclic reaction involved in the 1,5-electrocyclization of the UA mechanism.
通过基于异氰酸酯的多组分反应(IMCR)合成了一系列连接型 1,5-二取代四唑(1,5-DS-Ts),并以此为合成平台,在绿色条件下获得了含有环氧异吲哚-1(6H)-酮支架的结合型多杂环。这种快速声化学合成策略包括一个双多米诺过程,在乌基叠氮(UA)反应中使用一个正交杂环输入。通过 DFT 计算和 NBO 分析,我们了解了 UA 机理中 1,5 电环化所涉及的假环反应。
{"title":"Ultrasound-assisted diastereoselective green synthesis of spiro-fused-γ-lactams functionalized with an amide bond heterocyclic bioisostere via the Ugi azide/domino process coupled strategy†","authors":"David Calderón-Rangel, Ángel Rentería-Gómez, Alicia E. Cruz-Jiménez, Manuel A. Rentería Gómez, J. Oscar C. Jiménez-Halla and Rocío Gámez-Montaño","doi":"10.1039/D4OB00606B","DOIUrl":"10.1039/D4OB00606B","url":null,"abstract":"<p >A series of linked-type 1,5-disubstituted tetrazoles (1,5-DS-Ts) were synthesised <em>via</em> an isocyanide-based multicomponent reaction (IMCR) and used as synthetic platforms to access bound-type polyheterocycles containing an epoxyisoindol-1(6<em>H</em>)-one scaffold under green conditions. This rapid sonochemical synthetic strategy includes a double domino process using an orthogonal heterocyclic input in the Ugi-azide (UA) reaction. DFT calculations and NBO analysis were performed to understand the pseudopericyclic reaction involved in the 1,5-electrocyclization of the UA mechanism.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141329748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The chalcogen-bonding interactions formed at both sides of the thiocarbonyl group in thiourea were investigated. In particular, the role of these chalcogen-bonding interactions in the trans–trans conformation of thiourea was evaluated via single-crystal X-ray diffraction analysis and DFT calculations. The obtained results indicate that the Se⋯S⋯Se dual chalcogen-bonding interactions play a stronger role in controlling the planar structure than the S⋯S⋯S interactions.
研究人员对硫脲中硫代羰基两侧形成的缩醛键相互作用进行了研究。特别是通过单晶 X 射线衍射分析和 DFT 计算,评估了这些查尔根键相互作用在硫脲反式构象中的作用。结果表明,与 S⋯S⋯S 相互作用相比,Se⋯S⋯Se 双链键相互作用在控制平面结构方面发挥着更大的作用。
{"title":"Formation of chalcogen-bonding interactions and their role in the trans–trans conformation of thiourea†","authors":"Takumi Inoue, Nami Morita, Yui Amijima, Rika Sakai, Shohei Hamada, Seikou Nakamura, Yusuke Kobayashi and Takumi Furuta","doi":"10.1039/D4OB00723A","DOIUrl":"10.1039/D4OB00723A","url":null,"abstract":"<p >The chalcogen-bonding interactions formed at both sides of the thiocarbonyl group in thiourea were investigated. In particular, the role of these chalcogen-bonding interactions in the <em>trans</em>–<em>trans</em> conformation of thiourea was evaluated <em>via</em> single-crystal X-ray diffraction analysis and DFT calculations. The obtained results indicate that the Se⋯S⋯Se dual chalcogen-bonding interactions play a stronger role in controlling the planar structure than the S⋯S⋯S interactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob00723a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141425745","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiao-Ge Wang, Monday Peter Ajisafe, Eman Fayad, Hanadi A. Katouah and Hua-Li Qin
In this paper, the hydrogenation of aldehydes and ketones using the RANEY® nickel catalyst was successfully applied for the synthesis of alcohol compounds without additional column chromatographic purification. This synthetic strategy features a wide range of substrates, excellent atom economy, high chemical discrimination and the use of a ligand-free catalytic system. Reactions were performed at room temperature in water providing alcohols in high yields and purity.
{"title":"A protocol for hydrogenation of aldehydes and ketones to alcohols in aqueous media at room temperature in high yields and purity†","authors":"Xiao-Ge Wang, Monday Peter Ajisafe, Eman Fayad, Hanadi A. Katouah and Hua-Li Qin","doi":"10.1039/D4OB00798K","DOIUrl":"10.1039/D4OB00798K","url":null,"abstract":"<p >In this paper, the hydrogenation of aldehydes and ketones using the RANEY® nickel catalyst was successfully applied for the synthesis of alcohol compounds without additional column chromatographic purification. This synthetic strategy features a wide range of substrates, excellent atom economy, high chemical discrimination and the use of a ligand-free catalytic system. Reactions were performed at room temperature in water providing alcohols in high yields and purity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141316028","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}