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Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02363
Liang-Chen Ren, Min Wang, Xiao Zha, Yu-Rui Jian, Li-Ren Zhang, Jia-Jing Tan, Bao-Dong Cui, Yun Zhang, Xue-Qing Mou, Yong-Zheng Chen
{"title":"Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles","authors":"Liang-Chen Ren, Min Wang, Xiao Zha, Yu-Rui Jian, Li-Ren Zhang, Jia-Jing Tan, Bao-Dong Cui, Yun Zhang, Xue-Qing Mou, Yong-Zheng Chen","doi":"10.1021/acs.joc.4c02363","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02363","url":null,"abstract":"A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO<sub>2</sub>- and Ar<sub>2</sub>CN-functionalized <i>O</i>-heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH<sub>2</sub>- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions. Importantly, the efficient conversion of secondary alcohol products to amines with complete inversion of configuration enhances the methodology, enabling the construction of 2-aryl-3-amino tetrahydrofuran with high and complementary diastereoselectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857754","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
Competing Photocleavage on Boron and at the meso-Position in BODIPY Photocages
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02226
Ivan Ljubić, Igor Sviben, Vedran Brusar, Katarina Zlatić, Silvije Vdović, Nikola Basarić
{"title":"Competing Photocleavage on Boron and at the meso-Position in BODIPY Photocages","authors":"Ivan Ljubić, Igor Sviben, Vedran Brusar, Katarina Zlatić, Silvije Vdović, Nikola Basarić","doi":"10.1021/acs.joc.4c02226","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02226","url":null,"abstract":"BODIPY photocages (photocleavable protective groups) have stirred interest because they can release biologically active cargo upon visible light excitation. We conducted combined theoretical and experimental investigations on selected BODIPY photocages to elucidate the mechanism of the competing photocleavage at the boron and <i>meso</i>-position. Based on the computations, the former reaction involves elongation of the B–C bond, yielding a tight borenium cation and methyl anion. These ions are intercepted by CH<sub>3</sub>OH, enabling an efficient proton-coupled electron transfer (PCET) to produce the methane and isolated ether photoproducts. Singlet and triplet excited-state lifetimes were measured in CH<sub>3</sub>OH and CD<sub>3</sub>OD to probe the kinetic isotope effects (KIEs). The resulting KIEs are small, implying that the kinetic bottleneck is due to the C–B bond scission rather than the subsequent PCET. The introduction of a methoxy group in the <i>meso</i>-phenoxy substituent redirects the photosubstitution toward the <i>meso</i>-position. The corresponding regiochemistry was explained computationally. On elongating the C–O bonds in the S<sub>1</sub> state, it is found that the unproductive conical intersection is encountered much earlier for the alkyl–O bond than for the phenyl–O bond. The current findings are valuable for the rational design of new BODIPY photocages with tailored biological applications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857755","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
A Protocol for the Synthesis of Organophosphorus(V) Compounds with P–N and P–O Bonds by Umpolung Strategy Using Hydroxymethylphosphine Sulfides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c01832
Hidetoshi Ohta, Ryosuke Asahara, Ryusei Ikeda, Tateyuki Sakamoto, Minoru Hayashi
{"title":"A Protocol for the Synthesis of Organophosphorus(V) Compounds with P–N and P–O Bonds by Umpolung Strategy Using Hydroxymethylphosphine Sulfides","authors":"Hidetoshi Ohta, Ryosuke Asahara, Ryusei Ikeda, Tateyuki Sakamoto, Minoru Hayashi","doi":"10.1021/acs.joc.4c01832","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01832","url":null,"abstract":"Versatile P–N and P–O bond-forming reactions by an umpolung approach using air- and moisture-stable hydroxymethylphosphine sulfides were developed. Phosphine sulfides containing multiple hydroxymethyl groups could undergo sequential transformations combining P–N and P–O as well as P–C bond formations, providing a novel protocol for the synthesis of a variety of organophosphorus(V) compounds with P–N and P–O bonds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858135","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
New Frontiers in Nitramine Reactivity via the Mitsunobu Reaction
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02261
Aleksei B. Sheremetev, Pavel S. Gribov, Daniil A. Chernyshov, Dmitry L. Lipilin, Kyrill Yu. Suponitsky
{"title":"New Frontiers in Nitramine Reactivity via the Mitsunobu Reaction","authors":"Aleksei B. Sheremetev, Pavel S. Gribov, Daniil A. Chernyshov, Dmitry L. Lipilin, Kyrill Yu. Suponitsky","doi":"10.1021/acs.joc.4c02261","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02261","url":null,"abstract":"<i>N</i>-Nitro derivatives of primary alkyl, aryl and heteroarylamines can be directly alkylated with functionalized alcohols under Mitsunobu conditions at the <i>N</i> and/or <i>O</i> atoms of the nitramino moiety to give secondary nitramines or 1-alkoxydiazene 1-oxides, respectively.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857756","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
Visible-Light-Mediated Radical trans-Hydroboration of Alkynes with NHC Borane
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02577
Xin Wu, Zhang Chen, Xue Peng, Zhen Wang, Yao-Fu Zeng
{"title":"Visible-Light-Mediated Radical trans-Hydroboration of Alkynes with NHC Borane","authors":"Xin Wu, Zhang Chen, Xue Peng, Zhen Wang, Yao-Fu Zeng","doi":"10.1021/acs.joc.4c02577","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02577","url":null,"abstract":"Although the radical hydroboration of alkenes with N-heterocyclic carbene (NHC) borane is well documented, the radical hydroboration of alkynes, especially terminal alkynes, remains challenging. Herein, a photoredox-catalyzed radical <i>trans</i>-hydroboration of alkynes with NHC borane has been developed, which provided various alkenyl boron compounds in moderate to good yields. This protocol exhibits a broad substrate scope, as both internal and terminal alkynes were compatible. The synthetic value of this method was further demonstrated by its applicability in the late-stage modification of bioactive molecules. A preliminary mechanism for this reaction was proposed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857757","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
A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02413
Tarannum Tasnim, Negin Shafiei, Katelyn J. Laminack, Bailey S. Robertson, Nash E. Nevels, Christopher J. Fennell, Spencer P. Pitre
{"title":"A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides","authors":"Tarannum Tasnim, Negin Shafiei, Katelyn J. Laminack, Bailey S. Robertson, Nash E. Nevels, Christopher J. Fennell, Spencer P. Pitre","doi":"10.1021/acs.joc.4c02413","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02413","url":null,"abstract":"While charge-transfer complexes involving halogen-bonding interactions have emerged as an alternative strategy for the photogeneration of carbon radicals, examples using (fluoro)alkyl bromides are limited. This report describes a dual catalytic approach for radical generation from α-bromodifluoroesters and amides under visible-light irradiation. Mechanistic studies suggest that the reaction proceeds through <i>in situ</i> bromide displacement using a catalytic iodide salt, generating a C–I bond that can be engaged by our halogen-bonding photocatalysis platform.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849694","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
Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C–H Activation for the Synthesis of Fluorenones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c01956
Lei Gao, Min Wang, Hongwei Ren, Jinzhong Yao, Maozhong Miao, Hongwei Zhou
{"title":"Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C–H Activation for the Synthesis of Fluorenones","authors":"Lei Gao, Min Wang, Hongwei Ren, Jinzhong Yao, Maozhong Miao, Hongwei Zhou","doi":"10.1021/acs.joc.4c01956","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01956","url":null,"abstract":"An efficient method for construction of various fluorenones has been achieved via Rh(III)-catalyzed C–H activation/[4 + 2] annulation/aromatization sequences of simple and readily available enaminones and 1,3-dienes. This protocol showed good substrate compatibility as an array of structurally and electronically diverse fluorenones prepared efficiently in moderate to good yields and preparative scale utility showing very good efficiency in the late-stage functionalization of complex valuable molecules.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"261 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857758","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
Achieving Olympicene Functionalization Three Ways
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02471
Kaitlin M. Hartung, Ellen M. Sletten
{"title":"Achieving Olympicene Functionalization Three Ways","authors":"Kaitlin M. Hartung, Ellen M. Sletten","doi":"10.1021/acs.joc.4c02471","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02471","url":null,"abstract":"Polycyclic aromatic hydrocarbons (PAHs) and their derivatives are of interest in many fields, from materials science to supramolecular chemistry. 6<i>H</i>-Benzo[<i>cd</i>]pyrene, or olympicene, is a PAH bearing a central <i>sp</i><sup>3</sup>-carbon bridge. We sought methods to modify this center position while maintaining stable tetrahedral geometry. Here, we characterize reactivity patterns of three olympicene core starting materials, with two of the three leading to center functionalization of the olympicene core, including the first use of 5<i>H</i>-benzo[<i>cd</i>]pyren-5-one as an olympicene synthon.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"94 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849691","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
Dithiocarbamate as a Carbonyl Alternative in Pd-Catalyzed Carbonylative Homocoupling of Organoboronic Acids
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c01678
Manas Mondal, Amit Saha
{"title":"Dithiocarbamate as a Carbonyl Alternative in Pd-Catalyzed Carbonylative Homocoupling of Organoboronic Acids","authors":"Manas Mondal, Amit Saha","doi":"10.1021/acs.joc.4c01678","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01678","url":null,"abstract":"We have developed a novel protocol for carbonylative homocoupling of arylboronic acids using dithiocarbamate esters as the carbonyl alternative. A series of arylboronic acids underwent smooth reaction with dithiocarbamate ester (Me<sub>2</sub>NCS<sub>2</sub>Me) in the presence of Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub> catalyst, Cu(OAc)<sub>2</sub>·H<sub>2</sub>O additive, and Na<sub>2</sub>CO<sub>3</sub> in DCE solvent, producing the biaryl ketones efficiently. The mechanism has been studied with the help of several control experiments that reveal the probability of thioamide intermediacy. Chemoselective homocoupling allows the postsynthetic modification of the product.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"48 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857753","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
Correction to “Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores”
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02931
Allan F. C. Rossini, Ana Carolina A. Muraca, Gleison A. Casagrande, Cristiano Raminelli
{"title":"Correction to “Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores”","authors":"Allan F. C. Rossini, Ana Carolina A. Muraca, Gleison A. Casagrande, Cristiano Raminelli","doi":"10.1021/acs.joc.4c02931","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02931","url":null,"abstract":"For 1,2,11-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4<i>H</i>-dibenzo[<i>de</i>,<i>g</i>]quinoline (<b>5</b>), the correct <sup>1</sup>H and <sup>13</sup>C NMR data presented below should be considered instead of those presented in the original paper. In addition, for compound <b>5</b>, the correct <sup>1</sup>H NMR spectrum presented in the revised Supporting Information should be considered instead of that presented in the original Supporting Information. <sup>1</sup>H NMR (300 MHz, CDCl<sub>3</sub>) δ 7.19–7.13 (m, 1H), 6.85–6.81 (m, 2H), 6.57 (s, 1H), 3.81 (s, 3H), 3.80 (s, 3H), 3.53 (s, 3H), 3.05–2.94 (m, 3H), 2.87 (d, <i>J</i> = 13.4 Hz, 1H), 2.60 (dd, <i>J</i> = 16.2, 3.6 Hz, 1H), 2.47 (s, 3H), 2.44–2.35 (m, 2H); <sup>13</sup>C NMR (75 MHz, CDCl<sub>3</sub>) δ 156.7, 151.7, 145.5, 138.8, 128.6, 128.2, 127.2, 124.3, 121.2, 119.7, 110.9, 110.0, 62.9, 60.8, 55.8, 55.6, 52.9, 43.7, 35.8, 28.5. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02931. Copies of NMR spectra and single-crystal X-ray diffraction data (PDF) Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html. This article has not yet been cited by other publications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841798","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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