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Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-23 DOI: 10.1021/acs.joc.4c02193
Jinping Lan, Xiaolong Li, Mengyu Xu, Bin Zhang, Jin Luo, Yuan Zhou, Tao Wang
{"title":"Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides","authors":"Jinping Lan, Xiaolong Li, Mengyu Xu, Bin Zhang, Jin Luo, Yuan Zhou, Tao Wang","doi":"10.1021/acs.joc.4c02193","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02193","url":null,"abstract":"An efficient visible-light-induced radical carbon oximation of styrenes with 1-nitrosopyrrolidine and organic halides is developed. The reaction proceeds smoothly in the absence of a transition metal and a photocatalyst under mild conditions, producing a wide range of functionalized oximes in moderate to good yields. Mechanistic studies reveal that the reaction involves the generation of nucleophilic α-amino alkyl radicals and subsequent halogen atom transfer (XAT) with organic halides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"111 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874457","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
Reaction of 4-(Alkynyloxy)cyclohexa-2,5-dienones with Dimethyl Sulfoxide: A Catalyst-Free Formation of 6/5/3-Fused Tricyclic Enones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-23 DOI: 10.1021/acs.joc.4c02553
Archana Rai, Utpal Das
{"title":"Reaction of 4-(Alkynyloxy)cyclohexa-2,5-dienones with Dimethyl Sulfoxide: A Catalyst-Free Formation of 6/5/3-Fused Tricyclic Enones","authors":"Archana Rai, Utpal Das","doi":"10.1021/acs.joc.4c02553","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02553","url":null,"abstract":"6/5/3-Fused tricyclic enones were obtained when 4-(alkynyloxy)cyclohexa-2,5-dienones were treated with DMSO at 150 °C. The reaction proceeded via a four-membered oxathietene intermediate. The protocol developed is atom economical, has a broad substrate scope, and is amenable to gram-scale synthesis. The products obtained are susceptible to further synthetic transformations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874421","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
Binding of Bioactive Ammonium Ions in Water with a Cavity-Based Selectivity: Water Solubilization versus Micellar Incorporation
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-22 DOI: 10.1021/acs.joc.4c02610
Romain Carpentier, Caterina Testa, Andrea Pappalardo, Ivan Jabin, Kristin Bartik
{"title":"Binding of Bioactive Ammonium Ions in Water with a Cavity-Based Selectivity: Water Solubilization versus Micellar Incorporation","authors":"Romain Carpentier, Caterina Testa, Andrea Pappalardo, Ivan Jabin, Kristin Bartik","doi":"10.1021/acs.joc.4c02610","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02610","url":null,"abstract":"Many bioactive molecules contain primary ammonium groups, generating significant interest in developing selective receptors for ammonium ions. A promising strategy involves the use of polyaromatic cavitands to achieve size and shape selectivity through their cavity. However, designing effective receptors for ammonium ions in aqueous media is challenging due to the competitive nature of water. Calix[5]arenes are known to selectively bind primary ammonium ions over secondary, tertiary, and quaternary ammonium ions in organic solvents. Here, we report on the binding properties of a calix[5]arene, which bears carboxyl groups on its small rim, in organic solvents and aqueous media. This receptor was transferred in water either through deprotonation of its carboxyl groups or by incorporation into dodecylphosphocholine micelles. <sup>1</sup>H Nuclear Magnetic Resonance data confirmed the <i>endo</i> complexation of various primary ammonium ions in not only organic solvents but also both aqueous media. Cavity-based selectivity was also observed, validating the cavitand strategy for the selective binding of ammonium ions in water. Unique binding properties, driven by the calix[5]arene’s intrinsic recognition ability and the hydrophobic effect, were observed in water. Notably, binding affinities for dopamine and lysine derivatives with log <i>K</i><sub>a</sub> values of &gt;3.9 were determined. The direct solubilization of the receptor outperformed micellar incorporation due to the hydrophilic nature of the primary ammonium ions, which hinders their uptake into micelles. These results offer promising perspectives for the development of efficient chemosensors for the characterization of bioactive ammonium ions in water.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874511","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
One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-22 DOI: 10.1021/acs.joc.4c02459
Dung Tien Do
{"title":"One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones","authors":"Dung Tien Do","doi":"10.1021/acs.joc.4c02459","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02459","url":null,"abstract":"We have developed a simple and straightforward synthesis of chiral <i>spiro</i>-imidazolidinone cyclohexenones, featuring six contiguous stereocenters, from feedstock chemicals such as aminophenols, α,β-unsaturated aldehydes, and α-amino acids. Remarkably, this one-pot multicomponent reaction exhibits exceptional diastereoselectivity (&gt;20:1 dr) and relies solely on an amino acid precursor as the chiral source, avoiding the use of transition metals or additional organocatalysts. This reaction is efficient and scalable, enabling synthesis on a gram-scale.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"67 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874474","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
Naphthalene Hydrodearomatization via Controllable Photocatalytic Hydroboration
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-21 DOI: 10.1021/acs.joc.4c02732
Wengang Xu, Juan Tao, Yu-Qi Wang, Mingrui Liu, Fengyu Ma, Qiao Zhang, Feng-Lian Zhang, Mingbo Wu
{"title":"Naphthalene Hydrodearomatization via Controllable Photocatalytic Hydroboration","authors":"Wengang Xu, Juan Tao, Yu-Qi Wang, Mingrui Liu, Fengyu Ma, Qiao Zhang, Feng-Lian Zhang, Mingbo Wu","doi":"10.1021/acs.joc.4c02732","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02732","url":null,"abstract":"The photocatalytic dearomative 1,4-hydroboration of naphthalenes with an N-heterocyclic carbene borane (NHC-BH<sub>3</sub>) complex was reported herein with controllable regioselectivity and chemoselectivity. This protocol yielded a wide range of naphthalene derivatives bearing various functional groups, notably bioactive compounds. Hydroboration occurred through the cooperation of photoredox and hydrogen atom transfer via boryl radical addition to naphthalene and further selective protonation. Notably, tuning the conditions could lead to further hydrogenation of the tetrahydroboration products. Mechanistic studies, including experimental and computational studies, elucidated the mechanism for the regioselectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867611","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
Dehydrogenative Coupling of Alcohols with Hydrazines under Nickel Catalysis
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-21 DOI: 10.1021/acs.joc.4c02279
Reshma Babu, Abhijith Karattil Suresh, Rohit Kumar, Ekambaram Balaraman
{"title":"Dehydrogenative Coupling of Alcohols with Hydrazines under Nickel Catalysis","authors":"Reshma Babu, Abhijith Karattil Suresh, Rohit Kumar, Ekambaram Balaraman","doi":"10.1021/acs.joc.4c02279","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02279","url":null,"abstract":"The development of efficient and robust catalytic systems based on earth-abundant transition metals for fundamentally new transformations is crucial for sustainable chemical synthesis. Herein, an effective and selective Ni-catalyzed dehydrogenative coupling of alcohols with hydrazines with the liberation of ammonia gas is reported. Although several methods were documented for the <i>N</i>-alkylation reaction, the present strategy is conceptually novel, and the reaction proceeds through a pathway involving N–N bond cleavage of phenylhydrazine followed by hydrogen autotransfer. This unprecedented method demonstrates a wide substrate scope, allowing for the synthesis of C–N coupled products from arylhydrazines using various types of alcohols, including aryl, fused aryl, heteroaromatic, cyclic, and aliphatic alcohols, both primary and secondary alcohols. The present catalytic approach was expanded to facilitate selective deuterium incorporation reactions by employing deuterated alcohols at the α-methyl position of the resulting <i>N</i>-alkylated products. It is noteworthy that we have broadened the applicability of the current catalytic systems to facilitate the ketazine synthesis of hydrazine monohydrate by employing secondary alcohols. The reaction utilizes an inexpensive, abundant, and renewable alcohol that serves as both an alkylating and (transfer) hydrogenating agent. Kinetic studies reveal that the reaction rate depends on the concentration of arylhydrazine and the nickel catalyst, following fractional order.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"148 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867609","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
Conformational Analysis of Swallowtail Motifs in Porphyrins
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02059
Phuong-Lien Doan Cao, Khiem Chau Nguyen, Alexander A. Nevzorov, Milena Jovanovic, Phattananawee Nalaoh, Jonathan S. Lindsey
{"title":"Conformational Analysis of Swallowtail Motifs in Porphyrins","authors":"Phuong-Lien Doan Cao, Khiem Chau Nguyen, Alexander A. Nevzorov, Milena Jovanovic, Phattananawee Nalaoh, Jonathan S. Lindsey","doi":"10.1021/acs.joc.4c02059","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02059","url":null,"abstract":"Aqueous solubilization of porphyrins, often accomplished with appended polar aryl groups, can also be achieved with symmetrically branched alkyl (i.e., swallowtail) groups terminated with polar moieties. Here, carboxylic acids are employed as termini (versus prior phosphono- or phosphoester termini) in designs of <i>trans</i>-AB-porphyrins bearing a single swallowtail group (A) or <i>trans</i>-A<sub>2</sub>-porphyrins bearing two swallowtail groups. Variable-temperature <sup>1</sup>H NMR studies (−60 to 97 °C) revealed that the 4-heptanedioic acid group at the meso-position of the free base porphyrin rotates with rate constant 5 s<sup>–1</sup> (310 K) and Arrhenius energy barrier <i>E</i><sub>a</sub> = 11.5 kcal/mol, whereas an isopropyl group undergoes rotation ∼1000-times faster (<i>k</i> = 5770 s<sup>–1</sup>). The interconversion is sufficiently fast that conformational diastereomers, as when two such swallowtail groups are present in a <i>trans</i>-A<sub>2</sub>-porphyrin, would not be isolable at room temperature (Class I atropisomers). DFT calculations (4 porphyrins containing the isopropyl or 4-heptanedioic acid groups) showed that the lowest energy conformer contains the swallowtail C–H unit in the plane of the porphyrin. The presence of one or two 4-heptanedioic acid moieties imparted solubility of the porphyrin in phosphate-buffered saline (PBS). The results suggest applications in the life sciences where compact, aqueous-soluble porphyrins are desired.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"114 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857597","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
Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02439
Shruti Rajput, Rajat, Nitesh, Priya Gupta, Harpal Singh, Nidhi Jain
{"title":"Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light","authors":"Shruti Rajput, Rajat, Nitesh, Priya Gupta, Harpal Singh, Nidhi Jain","doi":"10.1021/acs.joc.4c02439","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02439","url":null,"abstract":"We report a visible-light-assisted tandem oxidative 5-<i>exo</i>-dig cyclization of 1,6-enynes for the synthesis of aminated C-3 aryloylated benzofuran, furopyridine, benzothiophene, and indole derivatives. The nitrogen-centered radical generated in situ from <i>N</i>-aminopyridinium salt initiates the consecutive formation of C–N, C–C, and C–O bonds. The methodology exhibits good functional group tolerance and regioselectivity, furnishing products in good to excellent yields at room temperature. Preliminary biological screening of synthesized molecules reveals their potential as anticancer agents.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"31 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857751","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
Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02320
Suman K. Saha, Anupriya Bera, Akanksha Kumari, Khyati Shukla, Nirmal K. Rana
{"title":"Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide","authors":"Suman K. Saha, Anupriya Bera, Akanksha Kumari, Khyati Shukla, Nirmal K. Rana","doi":"10.1021/acs.joc.4c02320","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02320","url":null,"abstract":"We report a cascade approach for the synthesis of 2,3-dihydropyrroles derivatives via a formal [4 + 1] annulation reaction of α,β-unsaturated imines with <i>in situ</i> generated pyridinium ylides. Importantly, this protocol is compatible with diverse substituted imines as well as pyridinium ylides, constructing 2,3-dihydropyrroles with excellent yield and selectivity. Thereafter, the Merrifield resin-supported pyridinium ylide as a potential C1 synthon was also employed in our strategy and reused several times, resulting in products with excellent yield and diastereoselectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"261 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857680","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
Formal Dearomative Hydroamination of 2-Arylphenols
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02654
Robert E. Wiley, Michael C. Eng, Aidan J. Clarkson, Jeffrey S. Johnson
{"title":"Formal Dearomative Hydroamination of 2-Arylphenols","authors":"Robert E. Wiley, Michael C. Eng, Aidan J. Clarkson, Jeffrey S. Johnson","doi":"10.1021/acs.joc.4c02654","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02654","url":null,"abstract":"An acid-promoted dearomative rearrangement of <i>O</i>-arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of <i>trans</i>-aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohexylamine scaffold in two steps (one purification) from commercially available or readily prepared 2-arylphenols.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858137","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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