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Photosensitized Imino-Sulfamoylation of Alkenes with Oxime Carbamates 烯与氨基甲酸肟的光敏亚胺磺化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01128
Ai-Lian Wang, Huan-Huan Zhao, Hao-Wen Jiang, Peng-Fei Xu
{"title":"Photosensitized Imino-Sulfamoylation of Alkenes with Oxime Carbamates","authors":"Ai-Lian Wang, Huan-Huan Zhao, Hao-Wen Jiang, Peng-Fei Xu","doi":"10.1021/acs.orglett.5c01128","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01128","url":null,"abstract":"In this study, we have devised a strategy that employs oxime carbamate as a bifunctional diamination reagent in combination with SO<sub>2</sub> to realize imino-sulfamoylation of alkenes. This protocol is characterized by its mild conditions, operational simplicity, and metal-free nature, while demonstrating broad functional group tolerance for alkenes. Furthermore, the application of this method provides an accessible route to a diverse range of β-amino sulfonamide derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897964","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
Strongly Oxidizing Thiapyrylium Salt for Organophotoredox Catalysis 强氧化噻吩盐在有机光氧化还原催化中的应用
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01080
Mohamed R. El-kholany, Takeru Senoo, Asuka Mizutani, Hiroyoshi Takamura, Takayoshi Suzuki, Isao Kadota, Kenta Tanaka
{"title":"Strongly Oxidizing Thiapyrylium Salt for Organophotoredox Catalysis","authors":"Mohamed R. El-kholany, Takeru Senoo, Asuka Mizutani, Hiroyoshi Takamura, Takayoshi Suzuki, Isao Kadota, Kenta Tanaka","doi":"10.1021/acs.orglett.5c01080","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01080","url":null,"abstract":"Photoredox catalysis has garnered significant attention in organic chemistry for its ability to promote chemical transformations under visible-light irradiation. To date, research on salt-based organophotoredox catalysts has mainly concentrated on the development of oxygen- and nitrogen-based catalysts such as acridinium and pyrylium salts, whereas sulfur-containing catalysts have received far less attention. Herein, we report a strongly oxidizing <i>tert</i>-butyl-substituted thiapyrylium organophotoredox catalyst (<sup><i>t</i></sup>Bu-TTPP) that exhibits a high excited-state reduction potential (<i>E</i><sub>1/2</sub>(C*/C<sup>•–</sup>) = +2.23 V vs SCE) and can be activated by blue LEDs. The <sup><i>t</i></sup>Bu-TTPP catalyst provided promising results in various photoredox reactions, such as radical-cation Diels–Alder reactions, trifluoromethylations, the [4 + 2] annulation of alkynes and thiophene, and the C–N cross-coupling of fluoroarenes, demonstrating its potential in photoredox catalysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"71 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893731","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
Chelating-Group-Assisted C(sp2)–O Reductive Elimination at the Gold(III) Center 螯合基团辅助C(sp2) -O在金（III）中心的还原消除
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01053
Avishek Das, Shivanshu Tripathi, Lisa Roy, Nitin T. Patil
{"title":"Chelating-Group-Assisted C(sp2)–O Reductive Elimination at the Gold(III) Center","authors":"Avishek Das, Shivanshu Tripathi, Lisa Roy, Nitin T. Patil","doi":"10.1021/acs.orglett.5c01053","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01053","url":null,"abstract":"Herein, we demonstrate chelating-group-assisted C(sp<sup>2</sup>)–O reductive elimination at gold(III) centers. Detailed stoichiometric studies highlighted the importance of a chelating group for achieving successful C–O reductive elimination, paving the way for the development of a catalytic version. The mechanistic investigations, including control experiments, <sup>31</sup>P NMR, mass spectrometry, and density functional theory (DFT) studies, suggested that the synergistic effect of the ligand and chelating group creates a highly coordinated environment around the Au(III) center to facilitate the C(sp<sup>2</sup>)–O bond-forming reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897960","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
Pyrone Isomerization Enabled Divergent Access to Multisubstituted Biaryl Phenol via Relay Claisen Rearrangement 吡咯酮异构化通过继电克莱森重排实现了对多取代联芳基苯酚的发散获取
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01077
Jialin Wang, Mingluo He, Tongxiang Cao, Shifa Zhu
{"title":"Pyrone Isomerization Enabled Divergent Access to Multisubstituted Biaryl Phenol via Relay Claisen Rearrangement","authors":"Jialin Wang, Mingluo He, Tongxiang Cao, Shifa Zhu","doi":"10.1021/acs.orglett.5c01077","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01077","url":null,"abstract":"Arene isomerization can simultaneously edit the arene backbone and its periphery, thereby bridging the independent chemistry of two distinct arenes. Herein, a facile pyrone isomerization approach for the divergent synthesis of five- and sixfold-substituted biaryl phenols is achieved by using a relay Claisen rearrangement as a crucial step. This catalyst-free isomerization reaction features high step, atom, and redox economy by transferring the innate oxidation state of pyrone into the biaryl phenols. Additionally, an intriguing self-activation phenomenon was observed, which enabled the selective dienone–phenol rearrangement of the aryl group.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897961","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
Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols camdoll衍生h -膦酸盐的立体选择性[1,2]-Phospha-Brook重排：α-三氟甲基醇的合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c00686
Ning Li, Qian Wu, Yu Huang, Junchen Li, Enxue Shi
{"title":"Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols","authors":"Ning Li, Qian Wu, Yu Huang, Junchen Li, Enxue Shi","doi":"10.1021/acs.orglett.5c00686","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00686","url":null,"abstract":"A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type of P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. A library of 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared to other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due to its unique center-chiral scaffold.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"138 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893730","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
Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions 金催化的C-S交叉偶联反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01321
Prafulla Bera, Tanmayee Nanda, Nayan A. Barhate, Manoj V. Mane, Nitin T. Patil
{"title":"Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions","authors":"Prafulla Bera, Tanmayee Nanda, Nayan A. Barhate, Manoj V. Mane, Nitin T. Patil","doi":"10.1021/acs.orglett.5c01321","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01321","url":null,"abstract":"Herein, we report the gold-catalyzed deallylative C–S cross-coupling reaction through ligand-enabled Au(I)/Au(III) redox catalysis. One of the major challenges in gold-catalyzed C–S cross-coupling reactions is to prevent catalyst deactivation caused by the formation of a strong gold–sulfur bond. We discovered that the use of allyl phenyl sulfide as a sulfur surrogate facilitates a dynamic equilibrium between cationic Au(I) and Au(I)-sulfide complexes, overcoming the gold quenching problem. A detailed mechanistic investigation, including <sup>31</sup>P NMR studies, mass analysis, and stoichiometric experiments, provided valuable insights into the reaction mechanism, which is further supported by computational studies.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893773","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
Nickel-Catalyzed Gas-Free Reductive Carbonylation of Aryl Thianthrenium Salts to Access Aryl Amides and Aryl Thioesters 镍催化芳基硫铵盐的无气还原羰基化制备芳基酰胺和芳基硫酯
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01203
Chen Chen, Lu-Yao Ding, Xiao-Xu Zhang, Guan-Shen Chen, Yan-Ping Zhu, Chunjie Ni, Bolin Zhu
{"title":"Nickel-Catalyzed Gas-Free Reductive Carbonylation of Aryl Thianthrenium Salts to Access Aryl Amides and Aryl Thioesters","authors":"Chen Chen, Lu-Yao Ding, Xiao-Xu Zhang, Guan-Shen Chen, Yan-Ping Zhu, Chunjie Ni, Bolin Zhu","doi":"10.1021/acs.orglett.5c01203","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01203","url":null,"abstract":"A nickel-catalyzed site-selective reductive carbonylation of arenes via aryl thianthrenium salts is described. Using Mo(CO)<sub>6</sub> as a convenient solid CO source and reductant and employing nitroarenes and sulfonyl chlorides as readily available nitrogen and sulfur sources, a range of aryl amides and aryl thioesters were successfully synthesized in moderate to good yields. The utility of this transformation is demonstrated through the synthesis of antimicrobial agents and the late-stage functionalization of biorelevant molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"95 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897965","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
Coupling of Acyl Radical Precursors with 2-Azaallyl Anions for the Synthesis of α-Amino Ketones 酰基前体与2-氮杂烯基阴离子偶联合成α-氨基酮
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01295
Haitao Yang, Yu Pan, Canli Zhang, Chen Chen, Haoqin Tang, Hongbin Zhang, Guogang Deng, Xiaodong Yang
{"title":"Coupling of Acyl Radical Precursors with 2-Azaallyl Anions for the Synthesis of α-Amino Ketones","authors":"Haitao Yang, Yu Pan, Canli Zhang, Chen Chen, Haoqin Tang, Hongbin Zhang, Guogang Deng, Xiaodong Yang","doi":"10.1021/acs.orglett.5c01295","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01295","url":null,"abstract":"A novel transition-metal-free radical coupling of 2-azaallyl anions for the synthesis of α-amino ketones has been developed. Easily accessible thioesters and 2-azaallyl anions undergo single electron transfer (SET) to generate acyl radicals, which participate in intermolecular radical coupling to generate α-amino ketones with good functional group tolerance and yields (31 examples, up to 98% yield). A telescoped gram-scale synthesis and derivatization of the product illustrate the potential synthetic utility of this method. Radical trapping and radical clock experiments support the proposed radical coupling pathway between the generated acyl radical and the 2-azaallyl radical.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897966","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
Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides 活化和未活化烯烃与（杂）芳基氯化物的区域选择性1,2-二（杂）芳基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01269
Yingjun Lan, Siqi Xie, Bin Liu
{"title":"Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides","authors":"Yingjun Lan, Siqi Xie, Bin Liu","doi":"10.1021/acs.orglett.5c01269","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01269","url":null,"abstract":"Aryl chlorides are more commercially available and lower cost compared with aryl bromides and iodides. However, the use of (hetero)aryl chlorides as aryl radical precursors for the di(hetero)arylation of alkenes remains an underdeveloped area. Furthermore, existing examples of theses reactions are predominantly confined to activated alkenes. In this study, we introduce a photoirradiation-promoted benzophenone-catalyzed 1,2-di(hetero)arylation process that is applicable to both activated and unactivated alkenes, utilizing (hetero)aryl chlorides and cyanoarenes as aryl sources. Importantly, this method allows for the simultaneous introduction of two heterocycles to alkenes with high regioselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897991","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
Ce(OTf)3-Catalyzed Asymmetric 6π Cyclization of Triaryldivinyl Ketones Ce(OTf)3催化三芳基二乙烯基酮的不对称6π环化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01081
Liu Li, Hao Wei, Zhanhui Yang, Jiaxi Xu
{"title":"Ce(OTf)3-Catalyzed Asymmetric 6π Cyclization of Triaryldivinyl Ketones","authors":"Liu Li, Hao Wei, Zhanhui Yang, Jiaxi Xu","doi":"10.1021/acs.orglett.5c01081","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01081","url":null,"abstract":"The rare-earth Ce(OTf)<sub>3</sub>-catalyzed asymmetric 6π cyclization of triaryldivinyl ketones is realized, affording methyl (<i>R</i>,<i>E</i>)-1-aryl-2-arylmethylidene-3-hydroxy-1,4-dihydronaphthalene-2-carboxylates in moderate to good yields with good to excellent enantioselectivities. The reaction provides a new strategy for the construction of optically active 3-hydroxy-1,4-dihydronaphthalene-2-carboxylic acid derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"56 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893728","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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