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From Established to Emerging: Evolution of Cross-Coupling Reactions. 从成熟到新兴：交叉偶联反应的演变。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02573
Mark R Biscoe, Josep Cornella, Dipannita Kalyani, Sharon Neufeldt
{"title":"From Established to Emerging: Evolution of Cross-Coupling Reactions.","authors":"Mark R Biscoe, Josep Cornella, Dipannita Kalyani, Sharon Neufeldt","doi":"10.1021/acs.joc.4c02573","DOIUrl":"10.1021/acs.joc.4c02573","url":null,"abstract":"","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16065-16069"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612801","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
2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts. 2,6-双（吡唑-1-基）吡啶 (1-bpp) 作为烷基吡啶鎓盐内姬石烷基化的通用配体。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-06-27 DOI: 10.1021/acs.joc.3c00665
Kristen M Baker, Olivia P Bercher, J Cameron Twitty, Thomas Mortimer, Mary P Watson
{"title":"2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts.","authors":"Kristen M Baker, Olivia P Bercher, J Cameron Twitty, Thomas Mortimer, Mary P Watson","doi":"10.1021/acs.joc.3c00665","DOIUrl":"10.1021/acs.joc.3c00665","url":null,"abstract":"<p><p>A Ni/1-bpp catalyst was demonstrated to be effective in the Negishi alkylation with multiple classes of alkylpyridinium salts, including α-primary and α-secondary. These conditions are also effective for benzylic pyridinium salts, demonstrating the successful Negishi alkylation of benzylic pyridinium salts for the first time. Further, 14 derivatives of 1-bpp were prepared with a variety of steric and electronic properties to study how these changes impact the success of the Negishi alkylation.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16249-16252"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9692092","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
Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides. 镍催化烷基胺衍生自由基前体与芳基碘化物的电诱导交叉亲电偶联。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-05-23 DOI: 10.1021/acs.joc.3c00859
Lars J Wesenberg, Alessandra Sivo, Gianvito Vilé, Timothy Noël
{"title":"Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides.","authors":"Lars J Wesenberg, Alessandra Sivo, Gianvito Vilé, Timothy Noël","doi":"10.1021/acs.joc.3c00859","DOIUrl":"10.1021/acs.joc.3c00859","url":null,"abstract":"<p><p>In recent years, the \"Escape-from-Flatland\" trend has prompted the synthetic community to develop a set of cross-coupling strategies to introduce sp<sup>3</sup>-carbon-based fragments in organic compounds. This study presents a novel nickel-catalyzed electrochemical methodology for reductive cross-electrophile coupling. The method enables C(sp<sup>2</sup>)-C(sp<sup>3</sup>) linkages using inexpensive amine-derived radical precursors and aryl iodides. The use of electrochemistry as a power source reduces waste and avoids chemical reductants, making this approach a more sustainable alternative to traditional cross-coupling methods.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16121-16125"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9512274","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 Regioselective Dehydrogenative Hydrazination of Tropones. 托品的高区域选择性脱氢肼化作用。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02358
Yan Wang, Muliang Zhang, Shi-Kai Tian
{"title":"Highly Regioselective Dehydrogenative Hydrazination of Tropones.","authors":"Yan Wang, Muliang Zhang, Shi-Kai Tian","doi":"10.1021/acs.joc.4c02358","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02358","url":null,"abstract":"<p><p>Direct C(sp<sup>2</sup>)-H bond functionalization of the tropone skeleton constitutes an atom-economical strategy to access substituted tropones that exist in some bioactive compounds. Herein, we report a convenient method for the preparation of 2-hydrazinotropones via C(sp<sup>2</sup>)-H bond functionalization. A variety of tropones participated in the dehydrogenative hydrazination reaction with hydrazine, delivering structurally diverse 2-hydrazinotropones in moderate to good yields with extremely high regioselectivity. This method is featured by operational simplicity and metal-free reaction conditions, thereby tolerating various functional groups.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637917","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
Expedited Aminoglutarimide C–N Cross-Coupling Enabled by High-Throughput Experimentation 通过高通量实验实现快速氨基戊二酰亚胺 C-N 交叉偶联
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02536
Jacqueline W. Gu, Martins S. Oderinde, Hui Li, Frederick Roberts, Jacob M. Ganley, Maximilian D. Palkowitz
{"title":"Expedited Aminoglutarimide C–N Cross-Coupling Enabled by High-Throughput Experimentation","authors":"Jacqueline W. Gu, Martins S. Oderinde, Hui Li, Frederick Roberts, Jacob M. Ganley, Maximilian D. Palkowitz","doi":"10.1021/acs.joc.4c02536","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02536","url":null,"abstract":"A simple protocol for the Buchwald–Hartwig cross-coupling of (hetero)aryl halides with unprotected aminoglutarimide to afford diverse cereblon binding motifs is disclosed. The development of this C–N cross-coupling method was enabled by high-throughput combinatory screening of solvents, bases, temperatures, and ligands. Scope studies revealed generality across various heteroaryl and aryl halides with the reaction proceeding under mild conditions. In comparison, this method demonstrated strategic superiority over previously reported approaches, as evidenced by a significant decrease in step count from known syntheses in the patent literature.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"246 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637773","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
Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters β,γ-不饱和酰胺与异铂衍生的 β,γ-不饱和 α-酮酯之间的不对称乙烯基迈克尔/六迈克尔串联反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02066
Shan-Shan Xu, Zi-Yu Li, Meng-Yu Liu, Feng Sha, Xin-Yan Wu
{"title":"Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters","authors":"Shan-Shan Xu, Zi-Yu Li, Meng-Yu Liu, Feng Sha, Xin-Yan Wu","doi":"10.1021/acs.joc.4c02066","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02066","url":null,"abstract":"An organocatalytic asymmetric vinylogous Michael/oxa-Michael tandem reaction between β,γ-unsaturated pyrazoleamides and isatin-derived β,γ-unsaturated ketoesters has been developed with excellent regio-, diastereo-, and enantioselectivities. The methodology provides an effective approach to construct enantiomerically pure 3,4′-pyranyl spirooxindole derivatives containing three contiguous chiral centers. Moreover, the transformations of the chiral products, including the removal and reduction of the pyrazole group, have been investigated.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637774","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
Access to Ketones via Nickel-Catalyzed Coupling between S-2-Pyridyl Thioesters and Redox-Active Esters Using an Organic Reductant 使用有机还原剂，通过镍催化 S-2-吡啶硫酯与氧化还原活性酯之间的偶联获得酮体
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c01242
Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Zheng Lin, Le Zhang, Jian Chen, Li Hai, Li Guo, Yong Wu
{"title":"Access to Ketones via Nickel-Catalyzed Coupling between S-2-Pyridyl Thioesters and Redox-Active Esters Using an Organic Reductant","authors":"Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Zheng Lin, Le Zhang, Jian Chen, Li Hai, Li Guo, Yong Wu","doi":"10.1021/acs.joc.4c01242","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01242","url":null,"abstract":"A nickel-catalyzed coupling between S-2-pyridyl thioesters and redox-active esters has been reported. Diludine was used as a reductant in this strategy. Our method rapidly achieves the target ketone products in moderate to good yield. The construction of nonanomeric C-acyl glycosides was realized through the approach as well.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637851","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
Diarenofuran[b]-fused BODIPYs: One-Pot SNAr-Suzuki Synthesis and Properties. 重 Renofuran[b]-fused BODIPYs: One-Pot SNAr-Suzuki Synthesis and Properties.
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02396
Limin He, Na Li, Yanqing Li, Yunxia Zhao, Shulin Gao, Zhaohui Wang, Xiangguang Li, Yanhua Yang, Wei Jiang
{"title":"Diarenofuran[<i>b</i>]-fused BODIPYs: One-Pot S<sub>N</sub>Ar-Suzuki Synthesis and Properties.","authors":"Limin He, Na Li, Yanqing Li, Yunxia Zhao, Shulin Gao, Zhaohui Wang, Xiangguang Li, Yanhua Yang, Wei Jiang","doi":"10.1021/acs.joc.4c02396","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02396","url":null,"abstract":"<p><p>We present a streamlined methodology that integrates regioselective tetrahalogen-BODIPY and <i>o</i>-hydroxyphenylboronic acid in a one-pot process, leveraging S<sub>N</sub>Ar nucleophilic substitution in conjunction with Suzuki coupling to afford diarenofuran [<i>b</i>]-fused BODIPYs (<b>DBFB1</b>-<b>9</b>) with commendable yields (85-95%) and short reaction times (0.5-1.0 h). X-ray structure analyses of <b>DBFB5</b>,<b>7-9</b> elucidate that these diarenofuran[<i>b</i>]-fused BODIPYs adopt a \"butterfly\" conformation, maintaining a highly rigid planarity. A comprehensive examination of the spectroscopic and electrochemical properties of these diarenofuran[<i>b</i>]-fused BODIPY derivatives, incorporating various substituents, reveals intriguing characteristics, including pronounced absorption and emission in the near-infrared region (NIR), elevated fluorescence quantum yields (Φ<sub>F</sub> = 75-89% in dichloromethane), and tunable HOMO-LUMO levels. Remarkably, compared to <b>DBFB1</b>-<b>8</b>, <b>DBFB9</b> possesses a large extended π-conjugated system, resulting in significant red shifts in its absorption and emission maxima, reaching 623 and 635 nm, respectively, and a reduced HOMO-LUMO gap. Despite this substantial structural expansion, <b>DBFB9</b> maintains a surprisingly high fluorescence quantum yield (Φ<sub>F</sub> = 80%), underscoring its exceptional photophysical performance and strong potential for applications requiring efficient NIR emission and robust fluorescence retention.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637916","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
Redox-Neutral Decarboxylative and Desulfonylative C(sp3) Trifluoromethylation: Method Development and Mechanistic Inquiry. 氧化还原中性脱羧和脱磺 C(sp3)三氟甲基化反应：方法开发与机理探究。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-07-19 DOI: 10.1021/acs.joc.3c00872
Chris M Seong, Courtney C Roberts
{"title":"Redox-Neutral Decarboxylative and Desulfonylative C(sp<sup>3</sup>) Trifluoromethylation: Method Development and Mechanistic Inquiry.","authors":"Chris M Seong, Courtney C Roberts","doi":"10.1021/acs.joc.3c00872","DOIUrl":"10.1021/acs.joc.3c00872","url":null,"abstract":"<p><p>Sodium triflinate (CF<sub>3</sub>SO<sub>2</sub>Na) is an inexpensive bench-stable radical CF<sub>3</sub> source that is often activated by external oxidants such as peroxides. However, despite the commercial accessibility of CF<sub>3</sub>SO<sub>2</sub>Na, the salt has never been applied to decarboxylative trifluoromethylation due to challenges in controlled cross-radical coupling. We report a redox-neutral approach to decarboxylative C(sp<sup>3</sup>) trifluoromethylation of carboxylic acid derivatives. Mechanistic inquiry is performed to address the limitations in scope.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16114-16120"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9837385","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
Masterpenoids A-D, Four Unprecedented Nortriterpenoids from the Mastic (Pistacia lentiscus) and Their Anti-inflammatory Activity. 从麝香草（Pistacia lentiscus）中提取的 Masterpenoids A-D, 四种前所未有的 Nortriterpenoids 及其抗炎活性。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-14 DOI: 10.1021/acs.joc.4c02281
Xuerui An, Wei Liu, Hengwei Zhou, Jiaxu Zhang, Yuwei Sun, Tianzhi Li, Wentian Xiang, Tao Yuan
{"title":"Masterpenoids A-D, Four Unprecedented Nortriterpenoids from the Mastic (<i>Pistacia lentiscus</i>) and Their Anti-inflammatory Activity.","authors":"Xuerui An, Wei Liu, Hengwei Zhou, Jiaxu Zhang, Yuwei Sun, Tianzhi Li, Wentian Xiang, Tao Yuan","doi":"10.1021/acs.joc.4c02281","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02281","url":null,"abstract":"<p><p>Four unprecedented nortriterpenoids, masterpenoids A-D, were isolated and fully elucidated from the resin of the mastic tree (<i>Pistacia lentiscus</i>). Masterpenoids A-C are the first norterpenoids featuring an unprecedented 6/6/6/10 ring system, while masterpenoid D possesses a novel 6/6/6/7/5 ring system. The anti-inflammatory potential of the compounds was meticulously assessed through the establishment of an in vitro model of lipopolysaccharide-induced inflammation in RAW264.7 macrophage cells. Among them, Masterpenoids A and D showed potent inhibition of NO production, with IC<sub>50</sub> values of 10.6 ± 0.8 and 8.2 ± 0.9 μM, respectively, compared to positive control dexamethasone (IC<sub>50</sub> = 23.2 ± 1.2 μM).</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612800","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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