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Image-Based Machine Learning Using Inkjet-Printed Chemicals: Mixing Ratio Prediction and Metal Ion Detection. 使用喷墨打印化学品的基于图像的机器学习：混合比例预测和金属离子检测。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-07-12 DOI: 10.1021/acs.orglett.5c02270
Taichi Sano,Yuki Terauchi,Yuki Ide,Ichigaku Takigawa,Tsuyoshi Minami,Yasuhide Inokuma
{"title":"Image-Based Machine Learning Using Inkjet-Printed Chemicals: Mixing Ratio Prediction and Metal Ion Detection.","authors":"Taichi Sano,Yuki Terauchi,Yuki Ide,Ichigaku Takigawa,Tsuyoshi Minami,Yasuhide Inokuma","doi":"10.1021/acs.orglett.5c02270","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c02270","url":null,"abstract":"Inkjet printing of π-conjugated organic compounds enabled rapid, low-cost generation of training images for the image-based machine learning (ML) prediction of mixing ratios. ML models with mean absolute errors below 4% were achieved within hours, even for dyes with subtle color differences. Changing the printing surface from filter paper to a polypropylene film extended the method to colorless compounds, including isomeric and macrocyclic systems. This approach also enabled spatial mapping of sub-microgram levels of Zn2+ ions using a weakly responsive colorimetric sensor, without the need for a spectrometer. This work demonstrates a simple, versatile strategy for integrating π-conjugated materials with ML in colorimetric sensing and mixture analysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
NBS-Promoted Synthesis of Maleimides by Oxidative Dearomatization of Pyrroles: Mechanistic Investigations Using Online MS in Real-Time. nbs催化吡罗氧化脱芳合成马来酰亚胺：实时在线质谱研究
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-07-12 DOI: 10.1021/acs.orglett.5c01976
Ankit Kumar,Pawan K Mishra,Abhijit Nandy,Ryan A Altman,Shibdas Banerjee,Akhilesh K Verma
{"title":"NBS-Promoted Synthesis of Maleimides by Oxidative Dearomatization of Pyrroles: Mechanistic Investigations Using Online MS in Real-Time.","authors":"Ankit Kumar,Pawan K Mishra,Abhijit Nandy,Ryan A Altman,Shibdas Banerjee,Akhilesh K Verma","doi":"10.1021/acs.orglett.5c01976","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01976","url":null,"abstract":"Oxidative dearomatization of pyrroles is an important organic transformation to deliver pharmaceutically important compounds, especially the synthesis of diaryl maleimides via the dearomatization of pyrroles has always been challenging. Herein, we report an unprecedented protocol for synthesizing functionalized maleimides by NBS-promoted oxidative dearomatization of 2,3,4-trisubstituted pyrroles. The reaction proceeds via three sequential reactions: dearomatization, oxidation, and detosylation. The use of online EI mass spectrometry has enabled the mechanistic analysis of the reaction by capturing several short-lived intermediates and monitoring the progress of the reaction in real-time.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612953","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Spiro[2.2]pentanes and Vinylcyclopropanes Using Sulfones as Carbene Equivalents. 以砜为碳当量合成螺[2.2]戊烷和乙烯基环丙烷。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-07-12 DOI: 10.1021/acs.orglett.5c02374
Charles Reece Teeples,Jobe Cabell Metts,John Douglas Johnson,Sidney M Wilkerson-Hill
{"title":"Synthesis of Spiro[2.2]pentanes and Vinylcyclopropanes Using Sulfones as Carbene Equivalents.","authors":"Charles Reece Teeples,Jobe Cabell Metts,John Douglas Johnson,Sidney M Wilkerson-Hill","doi":"10.1021/acs.orglett.5c02374","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c02374","url":null,"abstract":"Spiro[2.2]pentanes are rigid carbocycles with well-defined exit vectors and high F(sp3), which makes them intriguing functional groups for medicinal chemistry campaigns. The high degree of strain present in these compounds, however, precludes the use of traditional cyclopropanation methodologies for the synthesis of densely functionalized spiropentane derivatives, making them difficult to obtain. Herein, we report a strategy for the synthesis of substituted arylspiro[2.2]pentanes (16 examples, 24-81% isolated yield) using sulfones as carbene equivalents. During the study, an unexpected formal C-H insertion process was observed when utilizing cyclopropyl sulfone anions as cyclopropylidene equivalents (14 examples, 24-79% isolated yield). Deuterium-labeling studies suggest that the vinylcyclopropane products arise from a stepwise addition-elimination/isomerization pathway.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612950","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Edwin J. Gonzalez*, Sofia C. Santamarina, Anton Y. Khmelnitskiy, Ana L. Moore and Daniel A. Heredia*, 
{"title":"","authors":"Edwin J. Gonzalez*, Sofia C. Santamarina, Anton Y. Khmelnitskiy, Ana L. Moore and Daniel A. Heredia*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c02127","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595043","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Shisong Lv, Jin Li, Yuhui Hua, Jianfeng Wu, Junqiang Wang, Guohua Liu*, Lingling Li* and Rui Liu*, 
{"title":"","authors":"Shisong Lv, Jin Li, Yuhui Hua, Jianfeng Wu, Junqiang Wang, Guohua Liu*, Lingling Li* and Rui Liu*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c02037","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Yi Yi, Ankush Chakraborty, Xinliang Ding, Arvind Jaganathan, Neil Heberer and Babak Borhan*, 
{"title":"","authors":"Yi Yi, Ankush Chakraborty, Xinliang Ding, Arvind Jaganathan, Neil Heberer and Babak Borhan*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c01865","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595045","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Panyi Huang*, Ting He, Xinyu Li, Bin Sun and Yongmin Ma*, 
{"title":"","authors":"Panyi Huang*, Ting He, Xinyu Li, Bin Sun and Yongmin Ma*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c02518","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595047","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Rima Sengupta, Ryoya Nakajima, Yohei Haketa and Hiromitsu Maeda*, 
{"title":"","authors":"Rima Sengupta, Ryoya Nakajima, Yohei Haketa and Hiromitsu Maeda*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c02135","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595053","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11
Dong-Qing Yang, Xi-Ni Luo, Cuiyan Wu, Ming-Qi Yang, Jie-Xi Guo, Sheng Du, Ying Tong, Ke-Wei Lei*, Jun-Qi Zhang, Guo-Ping Ge* and Wen-Ting Wei*, 
{"title":"","authors":"Dong-Qing Yang, Xi-Ni Luo, Cuiyan Wu, Ming-Qi Yang, Jie-Xi Guo, Sheng Du, Ying Tong, Ke-Wei Lei*, Jun-Qi Zhang, Guo-Ping Ge* and Wen-Ting Wei*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 27","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5c02529","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595066","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chan-Evans-Lam Cu(II)-Catalyzed C-O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers. Cu（II）催化的C-O交叉偶联：拓宽功能化乙烯醚的合成途径。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-07-11 Epub Date: 2025-06-27 DOI: 10.1021/acs.orglett.5c01966
San L Pham, Frank E McDonald
{"title":"Chan-Evans-Lam Cu(II)-Catalyzed C-O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers.","authors":"San L Pham, Frank E McDonald","doi":"10.1021/acs.orglett.5c01966","DOIUrl":"10.1021/acs.orglett.5c01966","url":null,"abstract":"<p><p>We report a general and effective Cu(OAc)<sub>2</sub>-catalyzed C-O cross-coupling synthesis of di- and trisubstituted vinylic ethers, using a combination of <i>N</i>-isopropylimidazole ligand and dicumyl peroxide as stoichiometric oxidant. This method couples functionalized vinylic pinacolboronates with various 1° and 2° alcohols to provide single-step syntheses of novel and structurally complex vinylic ethers. The optimized conditions do not require excess alcohol reactant and substantially suppress competing side reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"7326-7330"},"PeriodicalIF":4.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144504208","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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