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Photocatalyst-Free Visible-Light-Mediated Synthesis of β-(Trifluoromethyl)alkenyl Ketoximes Using 2-Bromo-3,3,3-trifluoropropene as a Radical Precursor 以2-溴-3,3,3-三氟丙烯为自由基前体的无光催化-可见光介导合成β-（三氟甲基）烯基酮肟
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.orglett.6c03861
Yibo Shi, Ningning Gong, Xin Xin, Xiaobing Liu, Wenguang Li, Weiguang Kong, Yongqi Yu, Heyun Sheng, Ting Li
{"title":"Photocatalyst-Free Visible-Light-Mediated Synthesis of β-(Trifluoromethyl)alkenyl Ketoximes Using 2-Bromo-3,3,3-trifluoropropene as a Radical Precursor","authors":"Yibo Shi,&nbsp;Ningning Gong,&nbsp;Xin Xin,&nbsp;Xiaobing Liu,&nbsp;Wenguang Li,&nbsp;Weiguang Kong,&nbsp;Yongqi Yu,&nbsp;Heyun Sheng,&nbsp;Ting Li","doi":"10.1021/acs.orglett.6c03861","DOIUrl":"10.1021/acs.orglett.6c03861","url":null,"abstract":"<p>We report a photocatalyst-free, visible-light-mediateddifunctionalizationof alkenes employing 2-bromo-3,3,3-trifluoropropene (BTP) as a radicalprecursor. This protocol operates under mild conditions using potassiumformate as an electron transfer reagent and <em>tert</em>-butylnitrite (TBN) as a hydrogen atom transfer (HAT) reagent, enablingefficient β-(trifluoromethyl)alkenyl ketoxime synthesis. Notably,no photocatalyst or transition metal is required, yet excellent stereoselectivityof the conjugated terminal alkene is achieved. Furthermore, this methodexhibits a broad substrate scope and good functional group tolerance,accommodating diverse alkene classes.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13005–13010"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088056","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
Harnessing the Silicon Effect for Copper-Catalyzed Linear-E-Selective Reductive Coupling of Ketones with Allenylsilanes 利用铜催化酮与烯基硅烷线性选择性还原偶联的硅效应
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI: 10.1021/acs.orglett.6c03882
Qingbin Lu, Weixiang Ye, Yixiao Li, Baihui Gong, Shixin Zhang, Xuanyi Li, Aijun Lin, Shang Gao
{"title":"Harnessing the Silicon Effect for Copper-Catalyzed Linear-E-Selective Reductive Coupling of Ketones with Allenylsilanes","authors":"Qingbin Lu,&nbsp;Weixiang Ye,&nbsp;Yixiao Li,&nbsp;Baihui Gong,&nbsp;Shixin Zhang,&nbsp;Xuanyi Li,&nbsp;Aijun Lin,&nbsp;Shang Gao","doi":"10.1021/acs.orglett.6c03882","DOIUrl":"10.1021/acs.orglett.6c03882","url":null,"abstract":"<p>We report a copper-catalyzed reductive coupling of ketoneswithallenylsilanes that delivers γ-silyl homoallylic alcohols withexceptional linear <em>E</em>-selectivities. Mechanistic investigationsindicate that the silyl substituent functions as a directing elementfor regioselectivity control. DFT calculations further reveal thatthe allyl addition is the regio-determining step, where the branchedallylcopper species shows a markedly lower activation barrier. Thevinylsilane products serve as versatile platforms for downstream functionalization,enabling efficient carbon-chain elongation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13023–13028"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088575","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
Photoinduced (4 + 2) Annulation of ortho-Hydroxyphenyl-Substituted para-Quinone Methides with Diazocarbonyls: Diastereodivergent Synthesis of 4-Aryl-dihydrocoumarins 邻羟基苯基取代对醌甲醚与重氮羰基的光诱导（4 + 2）环化：4-芳基二氢香豆素的非对映发散合成
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c02908
Ke-Yin Yu, Xin-Yu Liu, Yu-Han Yang, Wenji Wang, Xian-Tao An, Jiwen Zhang, Chun-An Fan
{"title":"Photoinduced (4 + 2) Annulation of ortho-Hydroxyphenyl-Substituted para-Quinone Methides with Diazocarbonyls: Diastereodivergent Synthesis of 4-Aryl-dihydrocoumarins","authors":"Ke-Yin Yu,&nbsp;Xin-Yu Liu,&nbsp;Yu-Han Yang,&nbsp;Wenji Wang,&nbsp;Xian-Tao An,&nbsp;Jiwen Zhang,&nbsp;Chun-An Fan","doi":"10.1021/acs.orglett.6c02908","DOIUrl":"10.1021/acs.orglett.6c02908","url":null,"abstract":"<p>A novel photoinduced (4 + 2) annulation of <em>o</em>-hydroxyphenyl-substituted <em>p</em>-quinone methides withdiazocarbonyls, chemically initiatedby a photochemical Wolff rearrangement, is described. Remarkably,the diastereoselectivity of this reaction can be switched by employingeither TBAB/CaH<sub>2</sub> or H<sub>2</sub>O as an additive, establishingan effective diastereodivergent approach to synthetically importantfunctionalized 4-aryl-dihydrocoumarins.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12854–12860"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088626","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
Enantioselective Synthesis of Chiral 3-Substituted Tetrahydroquinolines via a Pd-Catalyzed C–C Cleavage/C–C Coupling Sequence 对映选择性：通过pd催化C-C裂解/ c -偶联序列合成手性3-取代四氢喹啉
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03823
Cheng-Yu Li, Xiao-Jing Liu, Zhen-Ting Mao, Yi-Xia Jia, Ren-Xiao Liang
{"title":"Enantioselective Synthesis of Chiral 3-Substituted Tetrahydroquinolines via a Pd-Catalyzed C–C Cleavage/C–C Coupling Sequence","authors":"Cheng-Yu Li,&nbsp;Xiao-Jing Liu,&nbsp;Zhen-Ting Mao,&nbsp;Yi-Xia Jia,&nbsp;Ren-Xiao Liang","doi":"10.1021/acs.orglett.6c03823","DOIUrl":"10.1021/acs.orglett.6c03823","url":null,"abstract":"<p>A palladium-catalyzedasymmetric synthesis of 3-substituted tetrahydroquinolines(THQs) through a C–C cleavage/C–C coupling sequencehas been developed. By employing Pd(OAc)<sub>2</sub>/Josiphos <strong>L7</strong> as the catalyst, an array of chiral tetrahydroquinolinesbearing a C3-ketone pendant was afforded in good to excellent yieldsand enantioselectivities by using 3-(2-bromoaniline)-tethered cyclobutanolsas substrates. Control experiments revealed that only <em>cis</em>-substrates were able to participate in the reaction. In addition,several synthetic transformations derived from the ketone moiety werecarried out to demonstrate the practical utility of this protocol.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12977–12982"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088723","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
Catalytic Desymmetrizing Carbonyl–Amine Condensation Reaction to Construct Axially Chiral Diaryl Ethers 催化脱对称羰基-胺缩合反应制备轴手性二芳醚
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.orglett.6c03721
Tao Huang, Ze-Xin Zhou, Hui-Ling Zhou, Xu-Ping Liu, Yan-Fei Niu, Yi-Yuan Peng, Qiu-Ping Ding, Xing-Ping Zeng
{"title":"Catalytic Desymmetrizing Carbonyl–Amine Condensation Reaction to Construct Axially Chiral Diaryl Ethers","authors":"Tao Huang,&nbsp;Ze-Xin Zhou,&nbsp;Hui-Ling Zhou,&nbsp;Xu-Ping Liu,&nbsp;Yan-Fei Niu,&nbsp;Yi-Yuan Peng,&nbsp;Qiu-Ping Ding,&nbsp;Xing-Ping Zeng","doi":"10.1021/acs.orglett.6c03721","DOIUrl":"10.1021/acs.orglett.6c03721","url":null,"abstract":"<p>Catalytic desymmetrizing carbonyl–amine condensation(CAC)reactions between prochiral 2,6-diamino diaryl ethers and cyclobutane-1,3-dioneshave been developed for the highly enantioselective synthesis of axiallychiral diaryl ethers in up to 99% ee values. This reaction representsthe first application of prochiral aromatic amines in catalyticallyasymmetric CAC reactions. Control experiments revealed that cyclobutane-1,3-dionesshowed an obviously higher reactivity and enantioselectivities inthese asymmetric CAC reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12947–12952"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088727","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
Molecular Spiral Staircases: Stepwise Construction of Multilayer Phenylene Stacks 分子螺旋阶梯：多层苯烟囱的逐步构建
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-08-25 DOI: 10.1021/acs.orglett.6c02890
Shuwei Ou, Jhih-Syong Jhang, Chih-hsiu Lin
{"title":"Molecular Spiral Staircases: Stepwise Construction of Multilayer Phenylene Stacks","authors":"Shuwei Ou,&nbsp;Jhih-Syong Jhang,&nbsp;Chih-hsiu Lin","doi":"10.1021/acs.orglett.6c02890","DOIUrl":"10.1021/acs.orglett.6c02890","url":null,"abstract":"<p>Stacked aromaticarchitectures represent important structural motifsin supramolecular chemistry, materials science, and molecular recognition.Herein, we report the modular synthesis of a series of covalentlylinked phenylene stacks containing up to six stacked phenylene unitsthrough consecutive Friedländer annulation reactions. The keystructural motif is a bay-substituted 6,7-dihydrodibenzo[<em>b</em>,<em>j</em>][4,7]phenanthroline (DHDBPT) scaffold, whichenforces close face-to-face arrangements between phenylene units.The resulting staircase-like architectures were characterized by spectroscopictechniques and single-crystal X-ray diffraction. Structural investigationsfurther demonstrated distinct stereochemical behavior across the oligomerseries. Odd-layer systems adopt <em>meso</em> configurations,whereas even-layer oligomers exhibit C2 chirality and can be resolved.The rotational barriers of terminal phenyl groups were shown to increasewith stack thickness, suggesting increasing cooperative rigidity withinthe densely packed aromatic framework.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12861–12866"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148822115","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
Dithiane-Enabled Divergent Ring Rearrangements for the Construction of Sulfur-Containing Semisaturated Fused Pyridines and Pyrroles 含硫半饱和熔融吡啶和吡咯的分散环重排
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.orglett.6c03956
Xiaomeng Gong, Guohong Tang, Yingying Xue, Rui-Peng Li, Shouchu Tang
{"title":"Dithiane-Enabled Divergent Ring Rearrangements for the Construction of Sulfur-Containing Semisaturated Fused Pyridines and Pyrroles","authors":"Xiaomeng Gong,&nbsp;Guohong Tang,&nbsp;Yingying Xue,&nbsp;Rui-Peng Li,&nbsp;Shouchu Tang","doi":"10.1021/acs.orglett.6c03956","DOIUrl":"10.1021/acs.orglett.6c03956","url":null,"abstract":"<p>Sulfur-containing semisaturated <em>N</em>-heterocyclesrepresent valuable three-dimensional drug-relevant scaffolds, yetgeneral divergent synthetic approaches remain scarce. Herein, we reporta metal-free <em>cis</em>-selective [3 + 2] cycloadditionbetween alkynyl 1,3-dithianes and 2<em>H</em>-azirines toconstruct strain-encoded bicyclic aziridine intermediates. The 1,3-dithianeunit functions as a sulfur shuttle that enables two reagent-controlledrearrangement pathways: Brønsted-acid-mediated ring expansionthrough 1,2-sulfur migration affords sulfur-functionalized semisaturatedfused pyridines, whereas oxidative Lewis-acid-promoted ring contractionfurnishes sulfur-functionalized semisaturated fused pyrroles.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13070–13075"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088066","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
Photoexcited Palladium-Catalyzed Defluorinative 1,2-Functional-Group Migration of Allylic Alcohols 光激发钯催化烯丙醇的去氟1,2官能团迁移
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03929
Xinyue Ma, Qianqian Li, Wei Sun, Zhijun Zuo
{"title":"Photoexcited Palladium-Catalyzed Defluorinative 1,2-Functional-Group Migration of Allylic Alcohols","authors":"Xinyue Ma,&nbsp;Qianqian Li,&nbsp;Wei Sun,&nbsp;Zhijun Zuo","doi":"10.1021/acs.orglett.6c03929","DOIUrl":"10.1021/acs.orglett.6c03929","url":null,"abstract":"<p>Interceptionof aryldifluoromethyl radicals by unactivated alkenesis typically limited to 1,2-difunctionalization. We report a photoexcitedpalladium-catalyzed defluoroalkylative rearrangement that combinesselective monodefluorination of trifluoromethylarenes, radical addition,local 1,2-migration, and carbonyl formation. The redox-neutral cascadeachieves formal 1,2,3-trifunctionalization of allylic alcohols, providingα-alkynyl, α-aryl, and α-heteroaryl β-(aryldifluoromethyl)ketones with broad functional-group compatibility and without stoichiometricoxidants, thereby redirecting postaddition alkyl radicals from conventionaltermination toward migration-enabled skeletal reorganization undervisible-light irradiation in a single operation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13064–13069"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088625","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
Deaminative Radical Sulfinylation Reaction 脱胺性垂直亚砜化反应
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03711
Juan Tang, Zhen-Fu Ke, En-Yin Yang, Mi Li, Xue-Qing Mou, Yun Zhang, Yong-Zheng Chen, Bao-Dong Cui
{"title":"Deaminative Radical Sulfinylation Reaction","authors":"Juan Tang,&nbsp;Zhen-Fu Ke,&nbsp;En-Yin Yang,&nbsp;Mi Li,&nbsp;Xue-Qing Mou,&nbsp;Yun Zhang,&nbsp;Yong-Zheng Chen,&nbsp;Bao-Dong Cui","doi":"10.1021/acs.orglett.6c03711","DOIUrl":"10.1021/acs.orglett.6c03711","url":null,"abstract":"<p>A straightforwardand efficient deaminative radical sulfinylationof primary amines has been established for the facile synthesis ofstructurally diverse sulfinamides. This transformation exploits commerciallyaccessible <em>O</em>-diphenylphosphinylhydroxylamine (DPPH)as a mild activator, enabling readily available alkyl and aryl primaryamines to serve as versatile radical precursors. These radical speciesefficiently couple with electrophilic sulfinylamine partners to furnisha broad spectrum of alkyl and aryl sulfinamides in generally moderateto good yields. The synthetic robustness and generality of this protocolare further demonstrated by late-stage functionalization of variouspharmaceutical scaffolds, scalable synthesis, and diversified downstreamderivatization of the obtained sulfinamide products. Mechanistic studiescorroborate a radical addition pathway as the plausible reaction mechanismunderlying this deaminative transformation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12928–12934"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088667","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
Rhodium-Catalyzed Asymmetric 1,4-Shift/Double-Cyclization Cascade for De Novo Synthesis of Spirolactones 铑催化的不对称1,4-移位/双环化级联重新合成螺旋内酯
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.orglett.6c03980
Jian Chen, Kai Xue, Qing-Xian Xie, Bo Wu, Yong-Gui Zhou
{"title":"Rhodium-Catalyzed Asymmetric 1,4-Shift/Double-Cyclization Cascade for De Novo Synthesis of Spirolactones","authors":"Jian Chen,&nbsp;Kai Xue,&nbsp;Qing-Xian Xie,&nbsp;Bo Wu,&nbsp;Yong-Gui Zhou","doi":"10.1021/acs.orglett.6c03980","DOIUrl":"10.1021/acs.orglett.6c03980","url":null,"abstract":"<p>A rhodium-catalyzed asymmetric 1,4-shift/double-cyclizationcascadeof alkyne-tethered ketoesters with arylboronic acids was disclosed.This sequence facilitates the <em>de novo</em> synthesis ofchiral spirolactones with high enantioselectivities and allows forthe formation of three chemical bonds and two rings in a single step.Moreover, synthetic applications of this protocol have been underscoredby diverse transformations that afford versatile chiral spirocycles.Mechanistic studies illustrate that this cascade involves a 1,4-rhodiumshift.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13088–13093"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088058","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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