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β-BoronEffect Enables RegioselectiveBaeyer–Villiger Oxidation for Selective C–C Bond Cleavage β-硼效应实现了区域选择性的baeyer - villiger氧化，用于选择性的C-C键裂解
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-16 DOI: 10.1021/acs.orglett.6c03751
Xinman Kang,Yifan Yang,Yin Li,Qingjiang Li,Honggen Wang
{"title":"β-Boron\u0000Effect Enables Regioselective\u0000Baeyer–Villiger Oxidation for Selective C–C Bond Cleavage","authors":"Xinman Kang,Yifan Yang,Yin Li,Qingjiang Li,Honggen Wang","doi":"10.1021/acs.orglett.6c03751","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03751","url":null,"abstract":"Abstract The Baeyer–Villiger oxidation is a fundamental transformation for converting ketones into esters, yet achieving high regioselectivity among structurally similar alkyl groups remains a longstanding challenge. Herein, we report a β-boron-directed strategy to control migratory selectivity in Baeyer–Villiger oxidations of alkyl ketones. This approach exploits the β-boron effect, wherein hyperconjugative interaction between the σ(C–B) bond and the adjacent σ*(C–C) orbital weakens the C–C bond and enhances its migratory aptitude. As a result, β-boryl ketones undergo highly regioselective rearrangement, overriding the classical migratory order. A broad range of β-MIDA boronate substrates are compatible with this protocol, enabling the efficient synthesis of diverse 1,2-amphiphilic building blocks. Mechanistic studies support the critical role of the β-boron effect in the migration step. Furthermore, preliminary results demonstrate that this effect can be extended to the Beckmann rearrangement, revealing boron as a versatile and previously underexplored directing group for controlling regioselectivity in rearrangement reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209517","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
MnBn(CO)5-Catalyzed Cascade C–HActivation/Annulation to Construct Bridged N -Heterocycles MnBn(CO)5催化级联c - h活化/环化构建桥接N -杂环
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-16 DOI: 10.1021/acs.orglett.6c04098
Yang Sun,Tiannan Wang,Nikolaos Kaplaneris,Zhijun Feng,Mengjiao Jiang,Dexiang Feng,Hui Wang,Lutz Ackermann,Zhiting Wang
{"title":"MnBn(CO)5-Catalyzed Cascade C–H\u0000Activation/Annulation to Construct Bridged\u0000 N\u0000 -Heterocycles","authors":"Yang Sun,Tiannan Wang,Nikolaos Kaplaneris,Zhijun Feng,Mengjiao Jiang,Dexiang Feng,Hui Wang,Lutz Ackermann,Zhiting Wang","doi":"10.1021/acs.orglett.6c04098","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04098","url":null,"abstract":"Abstract Herein, a manganese-catalyzed synthesis of bridged heterocycles via a C–H activation/annulation cascade between azomethine imines and Morita–Baylis–Hillman adducts is described. MnBn(CO)5 serves as a highly active catalyst, exhibiting unique and remarkable capability in C–H activation for this transformation. The reaction demonstrates broad substrate scope and good functional group tolerance, providing direct access to bridged pyrazolone frameworks under operationally simple and solvent-free conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"63 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209511","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
Photoredox-Catalyzed Difluoromethylation of Dehydroalanine and Dehydroalanine-Containing Dipeptides: A Proof-of-Concept Enantioselective Variant 光氧化还原催化脱氢丙氨酸和含脱氢丙氨酸二肽的二氟甲基化：概念验证的对映体选择性变体
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.orglett.6c03908
Yue Zhang, Hangzhi Jiang, Shengqun Zhang, Yiqian Li, Tianshuai Zhu, Guangwei Wu, Jing-Jing Zhang, Xingfeng Bai, Zhen Chen
{"title":"Photoredox-Catalyzed Difluoromethylation of Dehydroalanine and Dehydroalanine-Containing Dipeptides: A Proof-of-Concept Enantioselective Variant","authors":"Yue Zhang,&nbsp;Hangzhi Jiang,&nbsp;Shengqun Zhang,&nbsp;Yiqian Li,&nbsp;Tianshuai Zhu,&nbsp;Guangwei Wu,&nbsp;Jing-Jing Zhang,&nbsp;Xingfeng Bai,&nbsp;Zhen Chen","doi":"10.1021/acs.orglett.6c03908","DOIUrl":"10.1021/acs.orglett.6c03908","url":null,"abstract":"<p>A photoredox-catalyzed difluoromethylation of dehydroalanine(Dha)derivatives and protected Dha-containing dipeptides is described.The reaction enables direct installation of the CF<sub>2</sub>H groupto access β-difluoromethyl α-amino acid derivatives undermild conditions using difluoromethyl sulfone as the radical precursor.A proof-of-concept CPA-enabled enantioselective variant furnishedthe model product in 55% isolated yield and 73% ee. Mechanistic experimentssupport a radical–polar crossover pathway and suggest thatreversible product deprotonation may contribute to stereochemicalerosion.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13034–13039"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088059","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
Iodine-Mediated Oxidative N–N Bond Formations Providing Fused 1,2,3,5-Thiatriazole Derivatives from N-Pyridinyl Sulfonimidamides 碘介导的氧化N - N键的形成从N -吡啶基磺酰咪胺中提供融合的1,2,3,5-噻唑衍生物
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.orglett.6c03874
Chandan Chittapriya Sahu, Shulei Pan, Yijie Hu, Kari Rissanen, Carsten Bolm
{"title":"Iodine-Mediated Oxidative N–N Bond Formations Providing Fused 1,2,3,5-Thiatriazole Derivatives from N-Pyridinyl Sulfonimidamides","authors":"Chandan Chittapriya Sahu,&nbsp;Shulei Pan,&nbsp;Yijie Hu,&nbsp;Kari Rissanen,&nbsp;Carsten Bolm","doi":"10.1021/acs.orglett.6c03874","DOIUrl":"10.1021/acs.orglett.6c03874","url":null,"abstract":"<p>An iodine-mediated oxidative annulation of <em>N</em>-pyridylsulfonimidamides is reported, providing access to 2-substituted [1,2,3,5]thiatriazolo[3,4-<em>a</em>]pyridine 2-oxides through intramolecular N–N bondformation. This transition metal-free process offers a concise entryto bench-stable, highly heteroatom-rich sulfur(VI) heterocycles. Inaddition, divergent cyclizations during the preparation of alkyl sulfonimidamideprecursors afford structurally distinct sulfur(IV) thiadiazole derivatives.The results of radical-trapping experiments suggest a pathway viaan <em>N</em>-centered radical leading to cyclization followedby oxidative aromatization.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13000–13004"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088585","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
Palladium-Catalyzed Enantioselective Dearomative Domino Heck/Stille Reaction of Indoles 钯催化吲哚的对映选择性脱香DominoHeck/Stille反应
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.orglett.6c03404
Chuan-Jun Lu, Bing-Bing Huang, Fei Xie, Ren-Xiao Liang, Yi-Xia Jia, Ren-Rong Liu
{"title":"Palladium-Catalyzed Enantioselective Dearomative Domino Heck/Stille Reaction of Indoles","authors":"Chuan-Jun Lu,&nbsp;Bing-Bing Huang,&nbsp;Fei Xie,&nbsp;Ren-Xiao Liang,&nbsp;Yi-Xia Jia,&nbsp;Ren-Rong Liu","doi":"10.1021/acs.orglett.6c03404","DOIUrl":"10.1021/acs.orglett.6c03404","url":null,"abstract":"<p>Palladium-catalyzedenantioselective dearomative difunctionalizationof <em>N</em>-substituted indoles was developed via dearomativecarbonpalladation and subsequent capture of benzyl-Pd species by organostannanereagents (domino Heck/Stille reaction). A wide range of 2,3-disubstitutedchiral indolines bearing vicinal quaternary and tertiary stereocenterswas efficiently synthesized in one step with excellent enantioselectivitiesand diastereoselectivities.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12867–12872"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088610","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 2,3-Dihydro-4(1H)-pyrimidinones through Copper-Catalyzed Skeletal Rearrangement of Spirocyclic Aminimides 铜催化螺旋环氨基胺骨架重排合成2,3-二氢-4(1h)-嘧啶
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03996
Motohiro Yasui, Seinosuke Okumura, Shion Fujitomo, Nozomi Ogasawara, Takahiro Yamada, Norihiko Takeda, Masafumi Ueda
{"title":"Synthesis of 2,3-Dihydro-4(1H)-pyrimidinones through Copper-Catalyzed Skeletal Rearrangement of Spirocyclic Aminimides","authors":"Motohiro Yasui,&nbsp;Seinosuke Okumura,&nbsp;Shion Fujitomo,&nbsp;Nozomi Ogasawara,&nbsp;Takahiro Yamada,&nbsp;Norihiko Takeda,&nbsp;Masafumi Ueda","doi":"10.1021/acs.orglett.6c03996","DOIUrl":"10.1021/acs.orglett.6c03996","url":null,"abstract":"<p>Aminimides are known to act as nitrene equivalents throughN–Nbond cleavage in Curtius-type rearrangements, but their use in othernitrene-type transformations is largely unexplored. Herein, we reporta copper-catalyzed, atom-economical synthesis of 2,3-dihydro-4(1<em>H</em>)-pyrimidinones from alkynyl hydrazides. Control experimentssuggest that the transformation proceeds via cyclization to form spirocyclicaminimides, followed by N–N bond cleavage and intramolecularC–H insertion.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13098–13103"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088666","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
Thiourea-Catalyzed Glycosylation of C,N-Diaryl Glycosyl Imidates 硫脲催化C，N -二芳基糖基的糖基化
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03907
Shashiprabha Dubey, Pintu Kumar Mandal
{"title":"Thiourea-Catalyzed Glycosylation of C,N-Diaryl Glycosyl Imidates","authors":"Shashiprabha Dubey,&nbsp;Pintu Kumar Mandal","doi":"10.1021/acs.orglett.6c03907","DOIUrl":"10.1021/acs.orglett.6c03907","url":null,"abstract":"<p>We report a hydrogen bond-mediated glycosylation protocolemployinga new class of <em>C,N</em>-diaryl imidate glycosyl donorsbearing two <em>para</em>-fluorophenyl groups, enabling highlyefficient and stereoselective glycosylation across a broad range ofacceptors. A mechanistic study revealed that thiourea catalysts activatethe <em>C,N</em>-diaryl imidate glycosyl donors by forminga noncovalent donor-catalyst complex through hydrogen-bonds. Furthermore,the mild activation conditions and distinct reactivity of <em>C,N</em>-diaryl imidate glycosyl donors facilitate their applicationin various one-pot oligosaccharide synthesis strategies.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13040–13045"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088669","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
Mn-Mediated Cascade Cyclization of Isocyanides with Diaryphosphine Oxides: Access to Mono- and Bis-Heteroatom-Substituted Indolo[1,2-a]quinoxalines 锰介导的异氰酸酯与二磷氧化物级联环化：获得单和双杂原子取代的吲哚[1,2- a]喹啉
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI: 10.1021/acs.orglett.6c03963
Kaiwen Yi, Shichao Yang, Huanfeng Jiang, Jihui Gao, Wanqing Wu
{"title":"Mn-Mediated Cascade Cyclization of Isocyanides with Diaryphosphine Oxides: Access to Mono- and Bis-Heteroatom-Substituted Indolo[1,2-a]quinoxalines","authors":"Kaiwen Yi,&nbsp;Shichao Yang,&nbsp;Huanfeng Jiang,&nbsp;Jihui Gao,&nbsp;Wanqing Wu","doi":"10.1021/acs.orglett.6c03963","DOIUrl":"10.1021/acs.orglett.6c03963","url":null,"abstract":"<p>Herein, we report a novel manganese-mediated strategyfor the cascade cyclization of indole isocyanides with diarylphosphineoxides and water, enabling the one-step formation of heteroatom-richfused heterocycles via the simultaneous formation of C–C, C–O,and C–P bonds. This protocol features high regio- and chemoselectivities,mild conditions, operational simplicity, and broad functional grouptolerance. Mechanistic investigations support the involvement of aradical pathway in this transformation. The synthetic utility of thismethod is demonstrated through the late-stage functionalization andpreliminary biological evaluation of the newly formed products.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13082–13087"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088062","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
Atroposelective Desymmetrizing Iodination via Chiral Phosphoric Acid Catalysis: Synthesis of Axially Chiral Biaryl Phosphine Oxides 手性磷酸催化下的氨选择性去对称碘化：轴向手性联芳基膦氧化物的合成
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.orglett.6c03558
Yan Chang, Yushen Gao, Xinghua Wang, An-An Zhang, Mingliang Zhang, Gaowei Li, Bing-Bing Song, Yuan-Yuan Gao, Qiuling Song, Lantao Liu
{"title":"Atroposelective Desymmetrizing Iodination via Chiral Phosphoric Acid Catalysis: Synthesis of Axially Chiral Biaryl Phosphine Oxides","authors":"Yan Chang,&nbsp;Yushen Gao,&nbsp;Xinghua Wang,&nbsp;An-An Zhang,&nbsp;Mingliang Zhang,&nbsp;Gaowei Li,&nbsp;Bing-Bing Song,&nbsp;Yuan-Yuan Gao,&nbsp;Qiuling Song,&nbsp;Lantao Liu","doi":"10.1021/acs.orglett.6c03558","DOIUrl":"10.1021/acs.orglett.6c03558","url":null,"abstract":"<p>Herein, we report a CPA-catalyzed atroposelective iodinationofprochiral phosphine oxides bearing no hydrogen-bond-donor substituents,affording a range of 3′-iodinated axially chiral biaryl phosphineoxides in excellent yields and enantioselectivities. The reactionproceeds through synergistic noncovalent interactions among the iodinatingreagent, the catalyst, and the substrate, eliminating the need forsubstrate pre-functionalization or external additives. The methodaccommodates both di-<em>tert</em>-butyl and dicyclohexylphosphine oxide substrates, as well as diverse substitution patternson both aromatic rings.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12891–12897"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088065","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-Promoted Formal [4 + 3] Radical Annulation of Vinyldiazos: Access to Fluorinated Cyclohepta[b]indoles 可见光促进乙烯基重氮的正态[4 + 3]自由基环化：氟化环庚[b]吲哚的获取
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI: 10.1021/acs.orglett.6c03611
Xiang Li, Huijuan Huang, Yufei Zhang, Yecong Chang, Yi Li
{"title":"Visible-Light-Promoted Formal [4 + 3] Radical Annulation of Vinyldiazos: Access to Fluorinated Cyclohepta[b]indoles","authors":"Xiang Li,&nbsp;Huijuan Huang,&nbsp;Yufei Zhang,&nbsp;Yecong Chang,&nbsp;Yi Li","doi":"10.1021/acs.orglett.6c03611","DOIUrl":"10.1021/acs.orglett.6c03611","url":null,"abstract":"<p>Cyclohepta[<em>b</em>]indoles are important nitrogen-containingheterocycles, yet their efficient synthesis remains challenging. Herein,we report a visible-light-promoted formal [4 + 3] cyclization of 3-difluorobromoacetylindoleswith vinyldiazos through a photoredox cascade radical process. Thismethod provides straightforward access to a broad range of fluorinateddihydrocyclohepta[<em>b</em>]indole derivatives in good toexcellent yields. The reaction features mild conditions, broad substratescope, good functional-group tolerance, and operational simplicity.Gram-scale synthesis, product derivatizations, and late-stage modificationof complex bioactive molecules further demonstrate the synthetic utilityof this protocol.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12903–12909"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088577","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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