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Light-Mediated Direct Decarboxylative Giese Aroylations without a Photocatalyst
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02163
David M. Kitcatt, Eva Pogacar, Le Mi, Simon Nicolle, Ai-Lan Lee
Previous light-mediated approaches to the direct decarboxylative Giese aroylation reaction have mainly relied on the use of a photocatalyst and a reductive quenching pathway. By exploiting a mechanistically distinct oxidative protocol, we have successfully developed a photocatalyst-free, light-mediated direct Giese aroylation methodology.
{"title":"Light-Mediated Direct Decarboxylative Giese Aroylations without a Photocatalyst","authors":"David M. Kitcatt, Eva Pogacar, Le Mi, Simon Nicolle, Ai-Lan Lee","doi":"10.1021/acs.joc.4c02163","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02163","url":null,"abstract":"Previous light-mediated approaches to the direct decarboxylative Giese aroylation reaction have mainly relied on the use of a photocatalyst and a reductive quenching pathway. By exploiting a mechanistically distinct oxidative protocol, we have successfully developed a photocatalyst-free, light-mediated direct Giese aroylation methodology.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Concise Synthesis and Biological Evaluation of the Pyrrolo[4,3,2-de]quinoline Core of the Lymphostin Family
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02038
Chengsen Tian, Hongmin Li, Tingting Liu, Jiwei Xu, Haojie Guo, Xinyuan Zhang, Jiaojiao Yang, Jian Ning, Cheng Peng, Peng Jin, Lechao Cui, Yuqi Gao
The efficient synthesis of the pyrrolo[4,3,2-de]quinoline core of the lymphostin family (compound 1) has been accomplished in 7 steps and 18.6% overall yield, providing an efficient method for the total synthesis and structural modification of the lymphostin family. Compound 1 showed potent inhibitory activities against PI3K/mTOR in the nanomolar range and activity against human colorectal cancer cell lines comparable to that of oxaliplatin, which could be recognized as a novel lead compound for cancer therapy.
{"title":"Concise Synthesis and Biological Evaluation of the Pyrrolo[4,3,2-de]quinoline Core of the Lymphostin Family","authors":"Chengsen Tian, Hongmin Li, Tingting Liu, Jiwei Xu, Haojie Guo, Xinyuan Zhang, Jiaojiao Yang, Jian Ning, Cheng Peng, Peng Jin, Lechao Cui, Yuqi Gao","doi":"10.1021/acs.joc.4c02038","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02038","url":null,"abstract":"The efficient synthesis of the pyrrolo[4,3,2-<i>de</i>]quinoline core of the lymphostin family (compound <b>1</b>) has been accomplished in 7 steps and 18.6% overall yield, providing an efficient method for the total synthesis and structural modification of the lymphostin family. Compound <b>1</b> showed potent inhibitory activities against PI3K/mTOR in the nanomolar range and activity against human colorectal cancer cell lines comparable to that of oxaliplatin, which could be recognized as a novel lead compound for cancer therapy.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487115","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Computational Study of SmI2-Catalyzed Intermolecular Couplings of Cyclopropyl Ketones: Links between the Structure and Reactivity.
IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c01996
Song Yu, Ciro Romano, David J Procter, Nikolas Kaltsoyannis

SmI2-catalyzed intermolecular coupling reactions of cyclopropyl ketones with alkenes or alkynes offer an efficient strategy for furnishing diverse five-membered ring-containing molecular architectures. This study presents a systematic computational investigation to reveal the structure-reactivity relationships in these reactions. The reactivity of aryl cyclopropyl ketones is enhanced by the stabilized ketyl radical and cyclopropyl fragmentation, arising from the conjugation effect of the aryl ring, despite an obstacle emerging from the gauche styrene intermediate that elevates the energy barrier for radical trapping. By contrast, alkyl cyclopropyl ketones lack conjugation and exhibit high barriers for reduction and fragmentation but undergo facile radical trapping due to the minimal steric hindrance. Interestingly, ortho-substituted phenyl cyclopropyl ketones exhibit superior reactivity due to a balance between the moderate conjugation, promoting cyclopropyl fragmentation, and the pretwisted nature of the ortho-substituted phenyl that circumvents the hindrance posed by the gauche intermediate and facilitates the radical trapping. The markedly enhanced reactivity of bicyclo[1.1.0]butyl (BCB) ketones arises from facile fragmentation of the strained BCB motif. Bicyclo[2.1.0]pentyl (BCP) ketones, less strained than BCB ketones, are computationally verified to undergo efficient couplings with various partners, and this can be attributed to their stable fragmentation intermediates that facilitate radical trapping. Our findings provide insights that can aid in designing related reactions.

{"title":"Computational Study of SmI<sub>2</sub>-Catalyzed Intermolecular Couplings of Cyclopropyl Ketones: Links between the Structure and Reactivity.","authors":"Song Yu, Ciro Romano, David J Procter, Nikolas Kaltsoyannis","doi":"10.1021/acs.joc.4c01996","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01996","url":null,"abstract":"<p><p>SmI<sub>2</sub>-catalyzed intermolecular coupling reactions of cyclopropyl ketones with alkenes or alkynes offer an efficient strategy for furnishing diverse five-membered ring-containing molecular architectures. This study presents a systematic computational investigation to reveal the structure-reactivity relationships in these reactions. The reactivity of aryl cyclopropyl ketones is enhanced by the stabilized ketyl radical and cyclopropyl fragmentation, arising from the conjugation effect of the aryl ring, despite an obstacle emerging from the <i>gauche</i> styrene intermediate that elevates the energy barrier for radical trapping. By contrast, alkyl cyclopropyl ketones lack conjugation and exhibit high barriers for reduction and fragmentation but undergo facile radical trapping due to the minimal steric hindrance. Interestingly, <i>ortho</i>-substituted phenyl cyclopropyl ketones exhibit superior reactivity due to a balance between the moderate conjugation, promoting cyclopropyl fragmentation, and the pretwisted nature of the <i>ortho</i>-substituted phenyl that circumvents the hindrance posed by the <i>gauche</i> intermediate and facilitates the radical trapping. The markedly enhanced reactivity of bicyclo[1.1.0]butyl (BCB) ketones arises from facile fragmentation of the strained BCB motif. Bicyclo[2.1.0]pentyl (BCP) ketones, less strained than BCB ketones, are computationally verified to undergo efficient couplings with various partners, and this can be attributed to their stable fragmentation intermediates that facilitate radical trapping. Our findings provide insights that can aid in designing related reactions.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453478","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Oxadiazolone-Based Aromatic Annulations: A Nitrenoid Precursor for Tricyclic Aminoheterocycles
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c01622
W. Felix Zhu, Hanna M. Franz, Andreas Krämer, Emre Duman, Claire Empel, Michael W. Göbel, Rene M. Koenigs, Stefan Knapp, Kerstin Hiesinger, Ewgenij Proschak, Victor Hernandez-Olmos
Nitrogen-containing heterocycles are present in most approved drugs, reflecting the significance of their synthetic strategies. By utilizing oxadiazolone as a nitrenoid (nitrene-like) precursor, we have developed a general strategy for the annulation with nucleophilic heterocycles to access various polycyclic aminoheterocycles. We have discovered that 2-pyrryl-substituted substrates undergo a rearrangement, which indicates a spirocyclization–migration pathway. Given their fluorescence and biological activity as kinase hinge binders, these fragment-like aminoheterocycles represent potential starting points for applications in chemical biology and drug discovery.
{"title":"Oxadiazolone-Based Aromatic Annulations: A Nitrenoid Precursor for Tricyclic Aminoheterocycles","authors":"W. Felix Zhu, Hanna M. Franz, Andreas Krämer, Emre Duman, Claire Empel, Michael W. Göbel, Rene M. Koenigs, Stefan Knapp, Kerstin Hiesinger, Ewgenij Proschak, Victor Hernandez-Olmos","doi":"10.1021/acs.joc.4c01622","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01622","url":null,"abstract":"Nitrogen-containing heterocycles are present in most approved drugs, reflecting the significance of their synthetic strategies. By utilizing oxadiazolone as a nitrenoid (nitrene-like) precursor, we have developed a general strategy for the annulation with nucleophilic heterocycles to access various polycyclic aminoheterocycles. We have discovered that 2-pyrryl-substituted substrates undergo a rearrangement, which indicates a spirocyclization–migration pathway. Given their fluorescence and biological activity as kinase hinge binders, these fragment-like aminoheterocycles represent potential starting points for applications in chemical biology and drug discovery.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487113","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Synthetic Approach to Chromone and Flavonoid Piperidine Alkaloids
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c01926
Karen A. Guarneros-Cruz, Silvano Cruz-Gregorio, Julio Romero-Ibañez, Rosa L. Meza-León, Fernando Sartillo-Piscil
Despite the enormous importance of chromone and flavonoid piperidine alkaloids, a general method for their synthesis has not been described. Accordingly, from simple tetrahydro-3-pyridinemethanols (A) and phenol derivatives (B), a synthetic approach to chromone and flavonoid piperidine alkaloids is presented. The access to a novel chromone and flavonoid alkaloid precursors 4-(2-hydroxyphenyl)-3-methylenepiperidines (C) is achieved in only two steps: Mitsunobu reaction followed by an intramolecular C–H phenolization via an aromatic Claisen rearrangement of the respective Mitsunobu adducts (D). Consequently, the simultaneous installation of the functionalized phenol group and the exo-methylene group within the piperidine skeleton, permits, not only the easy construction of the chromone or flavonoid cores but also the simultaneous installation of the hydroxyl group with the required cis-orientation. Additionally, the synthetic utility of this novel approach is showcased in the formal synthesis of flavopiridol, rohitukine, and their N-Moc analogues.
{"title":"Synthetic Approach to Chromone and Flavonoid Piperidine Alkaloids","authors":"Karen A. Guarneros-Cruz, Silvano Cruz-Gregorio, Julio Romero-Ibañez, Rosa L. Meza-León, Fernando Sartillo-Piscil","doi":"10.1021/acs.joc.4c01926","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01926","url":null,"abstract":"Despite the enormous importance of chromone and flavonoid piperidine alkaloids, a general method for their synthesis has not been described. Accordingly, from simple tetrahydro-3-pyridinemethanols (<b>A</b>) and phenol derivatives (<b>B</b>), a synthetic approach to chromone and flavonoid piperidine alkaloids is presented. The access to a novel chromone and flavonoid alkaloid precursors 4-(2-hydroxyphenyl)-3-methylenepiperidines (<b>C</b>) is achieved in only two steps: Mitsunobu reaction followed by an intramolecular C–H phenolization via an aromatic Claisen rearrangement of the respective Mitsunobu adducts (<b>D</b>). Consequently, the simultaneous installation of the functionalized phenol group and the exo-methylene group within the piperidine skeleton, permits, not only the easy construction of the chromone or flavonoid cores but also the simultaneous installation of the hydroxyl group with the required <i>cis</i>-orientation. Additionally, the synthetic utility of this novel approach is showcased in the formal synthesis of flavopiridol, rohitukine, and their <i>N</i>-Moc analogues.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Ag(I)-Catalyzed Oxidative Cyclization of 1,4-Diynamide-3-ols with N-Oxide for Divergent Synthesis of 2-Substituted Furan-4-carboxamide Derivatives
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02096
Akshay Subhash Narode, Debashis Barik, Ping-Hsun Kuo, Mu-Jeng Cheng, Rai-Shung Liu
This work reports Ag(I)-catalyzed oxidative cyclizations of 1,4-diynamide-3-ols with 8-methylquinoline oxide to form 2-substituted furan-4-carboxamides. The reaction chemoselectivity is distinct from that reported in previous work by Hashmi. We performed density functional theory calculations to elucidate our proposed mechanism after evaluation of the energy profiles of two possible pathways. In this Ag(I) catalysis, the calculations suggest that the amide and alkyne groups of the 3,3-dicarbonyl-2-alkyne intermediates tend to chelate with the Ag(I) catalyst, further inducing a formyl attack at the Ag(I)-π-alkyne moiety to deliver the observed products.
{"title":"Ag(I)-Catalyzed Oxidative Cyclization of 1,4-Diynamide-3-ols with N-Oxide for Divergent Synthesis of 2-Substituted Furan-4-carboxamide Derivatives","authors":"Akshay Subhash Narode, Debashis Barik, Ping-Hsun Kuo, Mu-Jeng Cheng, Rai-Shung Liu","doi":"10.1021/acs.joc.4c02096","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02096","url":null,"abstract":"This work reports Ag(I)-catalyzed oxidative cyclizations of 1,4-diynamide-3-ols with 8-methylquinoline oxide to form 2-substituted furan-4-carboxamides. The reaction chemoselectivity is distinct from that reported in previous work by Hashmi. We performed density functional theory calculations to elucidate our proposed mechanism after evaluation of the energy profiles of two possible pathways. In this Ag(I) catalysis, the calculations suggest that the amide and alkyne groups of the 3,3-dicarbonyl-2-alkyne intermediates tend to chelate with the Ag(I) catalyst, further inducing a formyl attack at the Ag(I)-π-alkyne moiety to deliver the observed products.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487116","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Quinazoline-Derived Azomethine Imines as Substrates To Access Polycyclic Compounds 喹唑啉衍生偶氮甲胺作为获取多环化合物的底物
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02189
Li-Ming Zhao, Yu-Jiao Wang
Quinazolines are essential structural constituents of many pharmaceuticals and bioactive natural products. Quinazoline-derived azomethine imines (QAIs) have emerged recently as valuable building blocks for the synthesis of various quinazoline derivatives. This Synopsis presents recent advances in (formal) cycloaddition reactions of QAIs for the synthesis of quinazoline-fused 5- to 8-membered heterocycles as well as three-dimensional compounds.
喹唑啉类是许多药物和具有生物活性的天然产品的重要结构成分。最近，喹唑啉衍生的偶氮亚胺（QAIs）已成为合成各种喹唑啉衍生物的重要构件。本简介介绍了 QAIs 的（形式）环化反应在合成喹唑啉融合的 5 至 8 元杂环以及三维化合物方面的最新进展。
{"title":"Quinazoline-Derived Azomethine Imines as Substrates To Access Polycyclic Compounds","authors":"Li-Ming Zhao, Yu-Jiao Wang","doi":"10.1021/acs.joc.4c02189","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02189","url":null,"abstract":"Quinazolines are essential structural constituents of many pharmaceuticals and bioactive natural products. Quinazoline-derived azomethine imines (QAIs) have emerged recently as valuable building blocks for the synthesis of various quinazoline derivatives. This Synopsis presents recent advances in (formal) cycloaddition reactions of QAIs for the synthesis of quinazoline-fused 5- to 8-membered heterocycles as well as three-dimensional compounds.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Cage-Shaped Borate Catalysts Bearing Precisely Controlled Lewis Acidity and Their Application in Glycosylations 具有精确控制的路易斯酸度的笼形硼酸盐催化剂及其在糖基化中的应用
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c01706
Yoshiyuki Manabe, Yuya Tsutsui, Yosuke Tanaka, Yuka Yokoyama, Yuka Ikinaga, Tatsuya Nishitani, Kumpei Yano, Ryohei Miyagawa, Koichi Fukase, Akihito Konishi, Makoto Yasuda
Cage-shaped borates, whose Lewis acidity can be precisely modulated by the structural attributes of the triphenolic ligands, were employed as catalysts for glycosylation. Each cage-shaped borate displayed distinctive reactivity; thus, screening of the borate catalysts enabled controllable activation of glycosyl fluorides under mild conditions. Practical glycosylation was achieved by fine-tuning the Lewis acidity tailored to the substrate reactivity, thereby providing a versatile method applicable to the synthesis of complex glycans.
{"title":"Cage-Shaped Borate Catalysts Bearing Precisely Controlled Lewis Acidity and Their Application in Glycosylations","authors":"Yoshiyuki Manabe, Yuya Tsutsui, Yosuke Tanaka, Yuka Yokoyama, Yuka Ikinaga, Tatsuya Nishitani, Kumpei Yano, Ryohei Miyagawa, Koichi Fukase, Akihito Konishi, Makoto Yasuda","doi":"10.1021/acs.joc.4c01706","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01706","url":null,"abstract":"Cage-shaped borates, whose Lewis acidity can be precisely modulated by the structural attributes of the triphenolic ligands, were employed as catalysts for glycosylation. Each cage-shaped borate displayed distinctive reactivity; thus, screening of the borate catalysts enabled controllable activation of glycosyl fluorides under mild conditions. Practical glycosylation was achieved by fine-tuning the Lewis acidity tailored to the substrate reactivity, thereby providing a versatile method applicable to the synthesis of complex glycans.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
NHPI-Catalyzed Electro-Oxidation of Alcohols to Aldehydes and Ketones NHPI 催化的醛到醛和酮的电氧化反应
IF 4.354 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02007
Jianyou Zhao, Chengling Deng, Lanlan Zhang, Jiatai Zhang, Quanjin Rong, Fan Wang, Zhong-Quan Liu
A practical and recyclable electro-oxidation of alcohols to aldehydes and ketones by using N-hydroxyphthalimide (NHPI) as the catalyst is presented. Through an undivided pool, under constant current conditions, various alcohols can be oxidized to the corresponding aldehydes or ketones in a high yield. Compared with previous methods, this system has the following characteristics: (1) the catalyst, electrode, electrolyte, and solvent (mainly water) are recyclable; (2) it has many advantages such as mild reaction conditions, easy operation, and good tolerance of functional groups; and (3) it can be smoothly scaled up to kilogram-scale production.
{"title":"NHPI-Catalyzed Electro-Oxidation of Alcohols to Aldehydes and Ketones","authors":"Jianyou Zhao, Chengling Deng, Lanlan Zhang, Jiatai Zhang, Quanjin Rong, Fan Wang, Zhong-Quan Liu","doi":"10.1021/acs.joc.4c02007","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02007","url":null,"abstract":"A practical and recyclable electro-oxidation of alcohols to aldehydes and ketones by using <i>N</i>-hydroxyphthalimide (NHPI) as the catalyst is presented. Through an undivided pool, under constant current conditions, various alcohols can be oxidized to the corresponding aldehydes or ketones in a high yield. Compared with previous methods, this system has the following characteristics: (1) the catalyst, electrode, electrolyte, and solvent (mainly water) are recyclable; (2) it has many advantages such as mild reaction conditions, easy operation, and good tolerance of functional groups; and (3) it can be smoothly scaled up to kilogram-scale production.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486457","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF3-Substituted β-Aza-spiroindolines and β-Carbolines. Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides：选择性合成 CF3 取代的 β-Aza-spiroindolines 和 β-Carbolines。
IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry
Pub Date : 2024-10-22 DOI: 10.1021/acs.joc.4c02302
Luo-Rong Yuan, You Zi, Shun-Jun Ji, Xiao-Ping Xu

A mild approach for synthesizing CF3-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process has been clarified. The approach shows good generality and practical applicability, highlighting its effectiveness and versatility.

该研究报告采用了一种温和的方法，通过位点选择性自由基环化，从色胺衍生的异氰酸酯中合成 CF3 取代的 β-氮杂螺吲哚啉和 β-咔啉。阐明了 C2 取代基在选择性环化过程中的关键作用。该方法显示出良好的通用性和实际适用性，突出了其有效性和多功能性。
{"title":"Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF<sub>3</sub>-Substituted β-Aza-spiroindolines and β-Carbolines.","authors":"Luo-Rong Yuan, You Zi, Shun-Jun Ji, Xiao-Ping Xu","doi":"10.1021/acs.joc.4c02302","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02302","url":null,"abstract":"<p><p>A mild approach for synthesizing CF<sub>3</sub>-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process has been clarified. The approach shows good generality and practical applicability, highlighting its effectiveness and versatility.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453479","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
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