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Electrochemical [4+1] Annulation of N-(Arylsulfonyl)acrylamides with 1,3-Dicarbonyl Compounds via Multiple C–H Functionalization
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-11 DOI: 10.1021/acs.orglett.6c04666
Xin-Yao Liu,Gui-Fen Lv,Qing Sun,Jin-Heng Li,Yang Li
{"title":"Electrochemical [4+1] Annulation of N-(Arylsulfonyl)acrylamides with 1,3-Dicarbonyl Compounds via Multiple C–H Functionalization","authors":"Xin-Yao Liu,Gui-Fen Lv,Qing Sun,Jin-Heng Li,Yang Li","doi":"10.1021/acs.orglett.6c04666","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04666","url":null,"abstract":"A general electrochemical intermolecular cascade annulation between N-arylacrylamides and 1,3-dicarbonyl compounds through C(sp3)–H/C(sp2)–H functionalization and 1,4-aryl migration has been developed. This protocol employs 1,3-dicarbonyl compounds as C1 synthons that undergo [4+1] carboannulation, delivering diverse functionalized indanes with two distinct quaternary carbon centers under noble-metal- and external-oxidant-free conditions. Control experiments indicate that the reaction proceeds via a sequential cascade of oxidative C(sp3)–H cleavage to generate an alkyl radical, radical addition across the C═C bond, 1,4-aryl migration, a further oxidative C(sp3)–H cleavage to form another alkyl radical, [4+1] annulation, and deprotonation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"8 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374810","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
Double Electrophilic Borylative Cyclization of a Pyridine Core Enables a Narrowband Ultraviolet B/N/O MR-TADF Emitter
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-11 DOI: 10.1021/acs.orglett.6c04656
Yue Wang,Jie Li,Zhangli Cheng,Xi Zhang,Maike Lin,Lingwei Qu,Zebin Chen,Kai Wang,Jun Ye
{"title":"Double Electrophilic Borylative Cyclization of a Pyridine Core Enables a Narrowband Ultraviolet B/N/O MR-TADF Emitter","authors":"Yue Wang,Jie Li,Zhangli Cheng,Xi Zhang,Maike Lin,Lingwei Qu,Zebin Chen,Kai Wang,Jun Ye","doi":"10.1021/acs.orglett.6c04656","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04656","url":null,"abstract":"A pyridine-embedded boron/nitrogen/oxygen multiple-resonance emitter, tBuBOPy, was synthesized on gram scale via methoxy-directed tandem borylation at the pyridine C3 and C5 positions. The incorporation of pyridine blue-shifts the emission by preferentially stabilizing the highest occupied molecular orbital. It also modifies the excited-state character, reducing hole–electron overlap and lowering the singlet–triplet energy gap. As a result, tBuBOPy exhibits ultraviolet TADF at 383 nm, with an fwhm of 25 nm and a high PLQY of 89%.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"44 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374809","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
Visible-Light-Induced Povarov-Type Reaction of N-Alkyl Anthranilium Salts with Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-10 DOI: 10.1021/acs.orglett.6c04422
Jianming Liu,Yan Tang,Huiming Liang,Yanping Huo,Qian Chen,Xianwei Li,Yang Gao
{"title":"Visible-Light-Induced Povarov-Type Reaction of N-Alkyl Anthranilium Salts with Alkenes","authors":"Jianming Liu,Yan Tang,Huiming Liang,Yanping Huo,Qian Chen,Xianwei Li,Yang Gao","doi":"10.1021/acs.orglett.6c04422","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04422","url":null,"abstract":"Although numerous photocatalytic protocols have been established for the synthesis of tetrahydroquinolines, the development of synthetic systems independent of sophisticated and costly photocatalysts remains highly desirable. Herein, a photocatalyst-free, visible-light-induced Povarov-type reaction of N-alkyl anthranilium salts with alkenes is developed for the efficient construction of ortho-acyl-substituted tetrahydroquinoline scaffolds. This transformation proceeds via direct visible-light excitation of N-alkyl anthranilium salts to generate key iminium cation intermediates, which further undergo Povarov-type cyclization with alkenes. The reaction features simple and mild conditions, no requirement for external photocatalysts, and broad substrate compatibility. Moreover, this method provides a convenient strategy for accessing valuable deuterated nitrogen heterocycles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374807","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
De Novo Access to Persubstituted Benzene-Fused Benzosilacyclohexanes via Organocatalytic Benzannulation of 4-Dicyanomethylene-1,1-Disubstituted Silacyclohexanes 通过4-二氰亚甲基-1,1-二取代硅环己烷的有机催化苯并制得过取代苯-熔融苯并硅环己烷
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-10 DOI: 10.1021/acs.orglett.6c04367
Xiao-Zhou Xie,Xi-Yu Wang,Zhong-Wei Wu,Yaoyong Zeng,Longnong You,Lingjun Zheng,Guangying Chen,Lijia Wang,Jin-Sheng Yu
{"title":"De Novo Access to Persubstituted Benzene-Fused Benzosilacyclohexanes via Organocatalytic Benzannulation of 4-Dicyanomethylene-1,1-Disubstituted Silacyclohexanes","authors":"Xiao-Zhou Xie,Xi-Yu Wang,Zhong-Wei Wu,Yaoyong Zeng,Longnong You,Lingjun Zheng,Guangying Chen,Lijia Wang,Jin-Sheng Yu","doi":"10.1021/acs.orglett.6c04367","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04367","url":null,"abstract":"We report an organocatalytic domino benzannulation strategy for the facile synthesis of persubstituted benzene-containing quinoline-fused silacyclohexanes and sila-tetrahydronaphthalenes using 4-dicyanomethylene-1,1-disubstituted silacyclohexanes as silicon-containing building blocks. The utility of this methodology was further demonstrated by a gram-scale synthesis, diverse transformations, and the promising antiproliferative activity against HCT-116 cells, along with the ability to modulate lysosome-associated pathways and mitigate the level of proteotoxic aggregation. This work provides a modular route to previously inaccessible persubstituted benzene-fused silacyclohexanes, offering new opportunities for silicon-containing functional molecules in drug discovery and materials science.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368402","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
Unveiling Vinyl Radical–Ketone Coupling: Synthesis of Flavan-3-ols via β-Scission Suppression
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-10 DOI: 10.1021/acs.orglett.6c04149
Muskan,Akhilesh K. Verma
{"title":"Unveiling Vinyl Radical–Ketone Coupling: Synthesis of Flavan-3-ols via β-Scission Suppression","authors":"Muskan,Akhilesh K. Verma","doi":"10.1021/acs.orglett.6c04149","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04149","url":null,"abstract":"An unprecedented vinyl radical–ketone coupling has been achieved via intramolecular, metal- and oxidant-free cyclization, enabling direct C–C bond formation under superbasic conditions while preserving the alkene unit. This transformation overcomes a long-standing challenge in radical chemistry by enabling a pathway that avoids the rapid β-scission typically associated with alkoxy radicals. The reaction proceeds under operationally simple conditions to afford benzylidene flavan-3-ols in a single step, with a broad structural scope and broad functional group compatibility. Mechanistic insights were gained through the synthesis of deuterium-labeled analogues. Late-stage functionalization with bioactive drug molecules further highlights the synthetic utility of this methodology.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374877","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
Cu(I)–BINAP-Catalyzed Synthesis of β-Lactams via EnT-Driven 1, 5-HAT
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-10 DOI: 10.1021/acs.orglett.6c04550
Qiang Wang,Xiang Zou,Shu-Jia Wu,Lin-Lin Zheng,Si-Qi Feng,Xin-Ru Ma,Yi-Wei Wu,Long-Hui Qiu,Zhang-Long Yu,Yong-Min Liang,Xiao-Ji Wang
{"title":"Cu(I)–BINAP-Catalyzed Synthesis of β-Lactams via EnT-Driven 1, 5-HAT","authors":"Qiang Wang,Xiang Zou,Shu-Jia Wu,Lin-Lin Zheng,Si-Qi Feng,Xin-Ru Ma,Yi-Wei Wu,Long-Hui Qiu,Zhang-Long Yu,Yong-Min Liang,Xiao-Ji Wang","doi":"10.1021/acs.orglett.6c04550","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04550","url":null,"abstract":"We report a Cu(I)–BINAP-catalyzed, visible-light-induced cyclization of α,β-unsaturated amides to β-lactams. This protocol utilizes triplet energy transfer to trigger a key intramolecular 1,5-HAT for ring closure. By avoiding preactivated substrates, this method offers an efficient, mild route to strained heterocyclic motifs, demonstrating the synthetic utility of copper photocatalysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374878","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
Sulfate Radical Anion as a Bifunctional Reagent: Dual-Site Activation Enables Direct Dearomatization of Nonactivated Arenes to p-Quinols
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-10 DOI: 10.1021/acs.orglett.6c04117
Yifan Ma,Shuaishuai Yue,Shuo Guo
{"title":"Sulfate Radical Anion as a Bifunctional Reagent: Dual-Site Activation Enables Direct Dearomatization of Nonactivated Arenes to p-Quinols","authors":"Yifan Ma,Shuaishuai Yue,Shuo Guo","doi":"10.1021/acs.orglett.6c04117","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04117","url":null,"abstract":"Oxidative dearomatization (ODA) of arenes represents a powerful strategy for constructing highly functionalized p-quinol frameworks. However, conventional methods are limited to preactivated phenols. Herein, we report a sulfate radical anion (SO4•–)-enabled intermolecular ODA of simple arenes to p-quinols under mild conditions. Mechanistic studies suggest a dual-site activation mode, with SO4•– functioning as both radical oxidant and nucleophile. This work overcomes a key limitation of conventional ODA by extending it directly to nonactivated arenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"75 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374808","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
Synergistic Pd/Cu Catalysis for the Asymmetric Synthesis of Alkylidenecycloalkanes Bearing Axial and Central Chirality Pd/Cu协同催化不对称合成具有轴向和中心手性的烷基环烷烃
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04495
Congman Song,Shilong Cao,Zhiwen Cui,Xing He,Hao Xie,Duanyang Kong
{"title":"Synergistic Pd/Cu Catalysis for the Asymmetric Synthesis of Alkylidenecycloalkanes Bearing Axial and Central Chirality","authors":"Congman Song,Shilong Cao,Zhiwen Cui,Xing He,Hao Xie,Duanyang Kong","doi":"10.1021/acs.orglett.6c04495","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04495","url":null,"abstract":"Axially chiral alkylidenecycloalkanes constitute an underexplored class of nonbiaryl chiral frameworks, and catalytic methods for simultaneously constructing their axial chirality and a nonadjacent carbon stereocenter remain limited. Herein, we report a synergistic Pd/Cu-catalyzed asymmetric coupling of vinylcycloalkyl acetates with glycine-derived iminoesters that establishes 1,3-related axial and central chirality in a single transformation. Complementary activation of the electrophilic and nucleophilic partners enables stereoselective carbon–carbon bond formation, providing modular access to structurally diverse amino acid derivatives. The reaction accommodates substituted vinylcyclohexyl and vinylcyclobutyl acetates, as well as iminoesters incorporating complex, biologically relevant fragments. The synthetic utility of the products is demonstrated through their conversion into dipeptides, hydantoins, spirocycles, and urea derivatives. This approach expands access to nonbiaryl axially chiral scaffolds bearing an additional central stereogenic element.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"21 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368397","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
Isomerization-Controlled Dual-State Emission of Pyridyl Triazolopyridine Derivatives 吡啶基三唑吡啶衍生物异构化控制的双态发射
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04520
Camille Chériaux,Valérie Mazan,Anna M. Grabarz,Denis Jacquemin,Gilles Ulrich,Carlotta Figliola
{"title":"Isomerization-Controlled Dual-State Emission of Pyridyl Triazolopyridine Derivatives","authors":"Camille Chériaux,Valérie Mazan,Anna M. Grabarz,Denis Jacquemin,Gilles Ulrich,Carlotta Figliola","doi":"10.1021/acs.orglett.6c04520","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04520","url":null,"abstract":"The high-yielding two-step reaction synthesis of pyridyl triazolopyridine derivatives 1a–1e with substituents in positions C7 and C2′ is reported. All derivatives show intense blue fluorescence emission with excellent ΦF in acidic solution (up to 72%) and in their neutral solid state (up to 66%). The experimental results together with the theoretical calculations suggest that the isomerization reaction is detrimental to the emissive properties of these compounds because it favors the non-radiative de-excitation via fast molecular motion.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368297","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 Copper-Catalyzed Enantioselective Deoxygenative Alkynylation 光诱导铜催化的对映选择性脱氧炔基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04254
Chen Yang,Zunsheng Chen,Jianzhong Lu,Liuqing Chai,Chenwei Wang,He Zhang,Zhenyu Wang,Awad Ateia,Hongyu Wang,Dawei Wang,Qiong Chen,Guozhu Zhang,Rui Guo
{"title":"Photoinduced Copper-Catalyzed Enantioselective Deoxygenative Alkynylation","authors":"Chen Yang,Zunsheng Chen,Jianzhong Lu,Liuqing Chai,Chenwei Wang,He Zhang,Zhenyu Wang,Awad Ateia,Hongyu Wang,Dawei Wang,Qiong Chen,Guozhu Zhang,Rui Guo","doi":"10.1021/acs.orglett.6c04254","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04254","url":null,"abstract":"Deoxygenative coupling provides an attractive strategy for converting abundant alcohol feedstocks into value-added molecules. Despite recent advances, the enantioselective synthesis of chiral alkynes from alcohols and their derivatives remains elusive. Herein, we report a photoinduced copper-catalyzed asymmetric deoxygenative alkynylation of alcohol-derived xanthates with terminal alkynes. This strategy employs aryl iodides as aryl radical precursors to activate xanthate esters, with both the electronic and steric properties of the aryl iodide being critical for efficient aryl radical generation and productive transformation. The reaction proceeds under mild conditions and exhibits good functional-group tolerance. Mechanistic studies support a radical relay pathway involving aryl-radical-mediated xanthate activation and copper-catalyzed asymmetric alkynylation, wherein the photoexcited chiral copper acetylide serves a dual role as the photoactive species for aryl radical generation and the enantioselective catalyst for C(sp3)–C(sp) bond formation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368398","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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