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Nickel-Catalyzed Enantioselective Carbo-Carbonylation of Alkenes Using Formic Acid as a CO Surrogate: Access to Oxindoles Bearing Chiral Quaternary Carbon 以甲酸为CO替代物的镍催化烯烃的对映选择性碳羰基化反应：获得含手性季碳的氧吲哚
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-21 DOI: 10.1021/acs.orglett.6c04269
Krishnamoorthy Kathirvel,Govindasamy Sekar
{"title":"Nickel-Catalyzed Enantioselective Carbo-Carbonylation of Alkenes Using Formic Acid as a CO Surrogate: Access to Oxindoles Bearing Chiral Quaternary Carbon","authors":"Krishnamoorthy Kathirvel,Govindasamy Sekar","doi":"10.1021/acs.orglett.6c04269","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04269","url":null,"abstract":"Carbonylation reactions typically rely on toxic carbon monoxide gas, often under pressurized conditions. Herein, we report an enantioselective nickel-catalyzed carbonylative difunctionalization of activated olefins using formic acid as a safe and operationally simple CO surrogate under mild conditions. The reaction employs a chiral phosphine-based ferrocene ligand to furnish ester-functionalized oxindoles bearing stereogenic quaternary carbon centers in high yields and enantioselectivities. Isotopic-labeling and XPS studies support in situ CO generation and trapping by an alkyl-nickel intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"16 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221773","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 Charge-Transfer Complex-Mediated Decarboxylative Phosphoniumation 光诱导电荷转移复合物介导的脱羧磷酸化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c04068
Hailong He,Jiajin Chen,Hongyao Wang,Wenlong He,Tao Zhou,Zihao Chen,Zhiyan Xue,Qilong Wu,Ziyi Xu,Shuyang Liu,Yunhe Jin
{"title":"Photoinduced Charge-Transfer Complex-Mediated Decarboxylative Phosphoniumation","authors":"Hailong He,Jiajin Chen,Hongyao Wang,Wenlong He,Tao Zhou,Zihao Chen,Zhiyan Xue,Qilong Wu,Ziyi Xu,Shuyang Liu,Yunhe Jin","doi":"10.1021/acs.orglett.6c04068","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04068","url":null,"abstract":"Phosphonium salts are valuable intermediates in organic synthesis, but their preparation often requires harsh conditions and specific carbon precursors. Herein, we report a photoinduced decarboxylative phosphoniumation of redox-active esters (RAEs) for the direct synthesis of alkyl and benzyl phosphonium salts. A photoresponsive ternary charge-transfer complex (CTC) formed from NaI, tertiary phosphines, and RAEs enables the reaction under transition-metal- and external-photocatalyst-free conditions. The method tolerates diverse benzyl and aliphatic RAEs and tertiary phosphines, including commercial phosphine ligand frameworks, and enables the late-stage phosphoniumation of complex carboxylic-acid-derived substrates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"56 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221771","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 Phosphine-Enabled Direct δ-Addition of Substituted Allenoates to Nitroalkenes: A Route to 1,3-Dienes and 1,3,5-Trienes 催化磷化氢催化取代烯丙酸酯直接δ加成到硝基烯烃：一条生成1,3-二烯和1,3,5-三烯的途径
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c03903
Jinlong Li,Shulei Pan,Ning Wang,Kaiyun Liu,Jing Ren,Xinyu Long,Kaizhi Li
{"title":"Catalytic Phosphine-Enabled Direct δ-Addition of Substituted Allenoates to Nitroalkenes: A Route to 1,3-Dienes and 1,3,5-Trienes","authors":"Jinlong Li,Shulei Pan,Ning Wang,Kaiyun Liu,Jing Ren,Xinyu Long,Kaizhi Li","doi":"10.1021/acs.orglett.6c03903","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03903","url":null,"abstract":"Conjugated polyene represents a ubiquitous structural motif found in natural products and pharmaceutical agents. In this study, we demonstrate that γ-substituted allenoates can act as nucleophilic C4 synthon equivalents of dienes under phosphine catalysis, enabling their efficient addition with nitroalkenes to afford β-nitro 1,3-diene derivatives in moderate to good yields. This transformation features a remarkably broad substrate scope and good functional group compatibility, and it can be applied to the late-stage functionalization of complex natural product derivatives. The utility of the resulting β-nitro conjugated dienes is further demonstrated through subsequent transformations, affording a diverse library of conjugated triene compounds. A plausible reaction mechanism along with representative applications are also discussed.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"153 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221769","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
Structural Factors That Impact Thioimidate Isomerization and Peptide Backbone Conformation 影响硫咪酯异构化和肽主链构象的结构因素
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c04049
Dionicio N. Reyes V,Katharina Tucker,Brendan J. Wall,Emily A. O’Brien,Brett VanVeller
{"title":"Structural Factors That Impact Thioimidate Isomerization and Peptide Backbone Conformation","authors":"Dionicio N. Reyes V,Katharina Tucker,Brendan J. Wall,Emily A. O’Brien,Brett VanVeller","doi":"10.1021/acs.orglett.6c04049","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04049","url":null,"abstract":"Thioimidates exhibit an unusual conformational equilibrium among peptide backbone functional groups, often populating their trans and cis isomers in nearly equal amounts. Despite their growing use as intermediates for peptide backbone editing and macrocyclization, the structural factors governing this equilibrium have not been systematically characterized. Here, we combine NMR spectroscopy and DFT calculations to define the thermodynamics and kinetics of thioimidate isomerization in a series of model peptides. Remarkably, the near-parity trans/cis equilibrium and barrier to interconversion are largely insensitive to the steric bulk and stereochemistry of the amino acids flanking the thioimidate. In contrast, increasing the steric demand at the thioimidate S substituent produces the largest observed shift in the conformational equilibrium. This trend is consistent with the enrichment of the tentatively assigned cis isomer and suggests that the S substituent may provide a means to perturb the equilibrium. Calculations further support an isomerization mechanism involving rehybridization at nitrogen through a linear transition state rather than direct rotation about the formal C═N bond. The resulting sequence independence provides substantial flexibility in the placement of thioimidates within peptides, enabling the broad application of their dynamic conformational behavior in peptide synthesis and macrocyclization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221772","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
Iron-Catalyzed Electrochemical α-C(sp3) Sulfonylation of Ethers and Pyrrolidine Derivatives with Sulfonyl Chlorides 铁催化的乙醚和吡咯烷衍生物与磺酰氯的α-C（sp3）磺化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c03709
Mingyu Jiang,Fuqi Li,Bei Lei,Wen-Ya Zheng,Junshan Lai
{"title":"Iron-Catalyzed Electrochemical α-C(sp3) Sulfonylation of Ethers and Pyrrolidine Derivatives with Sulfonyl Chlorides","authors":"Mingyu Jiang,Fuqi Li,Bei Lei,Wen-Ya Zheng,Junshan Lai","doi":"10.1021/acs.orglett.6c03709","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03709","url":null,"abstract":"Selective α-C(sp3) sulfonylation of ethers and nitrogen heterocycles provides atom- and step-economical access to aliphatic sulfones, which are prevalent building blocks in pharmaceuticals and fine chemicals. Organic electrosynthesis and iron catalysis represent sustainable synthetic platforms for radical C–S bond formation, yet their combination for aliphatic α-C(sp3) sulfonylation remains underexplored. Herein, an undivided-cell iron-catalyzed electrochemical α-sulfonylation of ethers and N-protected pyrrolidines with sulfonyl chlorides is reported. The method benefits from traceless electrical redox equivalents, a cheap earth-abundant catalyst, and broad functional group compatibility. Gram-scale reactions and product derivatizations demonstrate its synthetic practicability. This electro-driven protocol leverages an anodic Fe(III)/Fe(II) redox shuttle to generate ethers and pyrrolidine derivatives as substrate-derived radical cation intermediates, with sulfonyl radicals originating from direct cathodic reduction of sulfonyl chlorides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"225 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221775","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
Stereodivergent Access to E- and Z-Vinylated Oxindoles via Pd-Catalyzed C(sp3)–H Activation/Heck Coupling, and Energy-Transfer Catalysis 通过pd催化的C(sp3) - h活化/Heck偶联和能量转移催化获得E-和z -乙烯基氧吲哚
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c04320
Saleem Hafeez,Naveen Sihag,Dhanni,M Ramu Yadav
{"title":"Stereodivergent Access to E- and Z-Vinylated Oxindoles via Pd-Catalyzed C(sp3)–H Activation/Heck Coupling, and Energy-Transfer Catalysis","authors":"Saleem Hafeez,Naveen Sihag,Dhanni,M Ramu Yadav","doi":"10.1021/acs.orglett.6c04320","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04320","url":null,"abstract":"A one-pot stereodivergent strategy for synthesizing E- and Z-vinylated oxindoles has been developed using a Pd-based tandem catalysis and Pd/Ir relay catalysis. The Pd(0)-catalyzed tandem sequence features a cyclization/C(sp3)–H activation/intermolecular Heck coupling to afford the E-isomer in high yields with excellent stereoselectivities. Integration of this transformation with an Ir-based energy-transfer process in a relay-catalytic mode enables access to the geometrically challenging Z-isomer. The broad substrate scope, late-stage functionalization of bioactive molecules, and synthetic derivatization highlight the method’s utility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221768","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
TfOH/HFIP Cluster-Promoted Divergent C–C Bond Cleavage and Reconstruction of Alkynoic Acids TfOH/HFIP簇促进异构C-C键的断裂和重构
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-20 DOI: 10.1021/acs.orglett.6c04105
Yilin Xing,Xinyu Song,Yuanyuan Liu,Wanting Fu,Xuannai Wang,Yuanli Ding,Zikun Wang
{"title":"TfOH/HFIP Cluster-Promoted Divergent C–C Bond Cleavage and Reconstruction of Alkynoic Acids","authors":"Yilin Xing,Xinyu Song,Yuanyuan Liu,Wanting Fu,Xuannai Wang,Yuanli Ding,Zikun Wang","doi":"10.1021/acs.orglett.6c04105","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04105","url":null,"abstract":"C–C bond cleavage and reconstruction of carboxylic acids is predominantly directed at the C–C(O) position. Herein, we have successfully developed a TfOH/HFIP cluster-promoted divergent strategy for the C–C bond cleavage of alkynoic acids and their subsequent reconstruction with arenes, affording selective access to distinct molecular architectures through tunable decarboxylation or deketonation. This platform not only facilitates mild decarboxylative functionalization but also establishes an unprecedented deketonative functionalization pathway for carboxylic acids.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149221770","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
Oxidative Phosphorylation of Silyl Enol Ethers with H-Phosphine Oxides via Dual Cobaloxime and Photoredox Catalysis 双钴肟光氧化还原催化下硅烯醚与h -膦氧化物的氧化磷酸化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-19 DOI: 10.1021/acs.orglett.6c03987
Yong-Hao Ma,Wei Shi,Jing Wu,Xuefei Zhao,Teck-Peng Loh,Xu-Hong Hu
{"title":"Oxidative Phosphorylation of Silyl Enol Ethers with H-Phosphine Oxides via Dual Cobaloxime and Photoredox Catalysis","authors":"Yong-Hao Ma,Wei Shi,Jing Wu,Xuefei Zhao,Teck-Peng Loh,Xu-Hong Hu","doi":"10.1021/acs.orglett.6c03987","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03987","url":null,"abstract":"We report herein a visible-light-induced dual catalytic system merging cobaloxime and photoredox catalysis that enables the oxidative phosphorylation of silyl enol ethers with H-phosphine oxides. This method provides efficient access to diverse β-ketophosphine oxides, bypassing the need for external oxidants, harsh conditions, or a restricted substrate scope that typically plagues conventional methods. Salient features include easily accessible starting materials, broad functional group compatibility, late-stage modifications, and scalability. Mechanistic studies reveal that this formal oxidative phosphorylation of ketones proceeds via a phosphinoyl radical intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210916","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
Engineering Size-Complementary Alcohol Dehydrogenase Mutants for Highly Stereoselective Synthesis of Bulky Diaryl and Aliphatic Diols 高立体选择性合成大体积二芳基和脂肪族二醇的工程尺寸-互补醇脱氢酶突变体
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-19 DOI: 10.1021/acs.orglett.6c03975
Cheng-Long Xu,Lin-Lin Song,Meng-Jiao Li,Shu-Yun Ju,Zhe Dou,Ya-Jun Wang
{"title":"Engineering Size-Complementary Alcohol Dehydrogenase Mutants for Highly Stereoselective Synthesis of Bulky Diaryl and Aliphatic Diols","authors":"Cheng-Long Xu,Lin-Lin Song,Meng-Jiao Li,Shu-Yun Ju,Zhe Dou,Ya-Jun Wang","doi":"10.1021/acs.orglett.6c03975","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03975","url":null,"abstract":"Chiral 1,4-diols serve as crucial intermediates in the pharmaceutical industry, yet their asymmetric synthesis remains challenging. Through size-complementary engineering of alcohol dehydrogenase from Saccharomyces kudriavzevii, bulky diaryl and aliphatic chiral 1,4-diols were synthesized with high stereoselectivity. Mutant M5 showed a 181-fold enhancement in catalytic efficiency toward 1,4-diphenyl-1,4-butanedione, whereas mutant N2 delivered a space–time yield of 1065 g L–1 d–1 for (2S,5S)-hexanediol. This work provides a valuable platform for accessing bulky diaryl and aliphatic diols.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"73 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210908","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
Fluoindeneacids A and B: Antioxidant Cyclopentane-Containing Molecules with Enzyme-Triggered Nonenzymatic Skeletal Rearrangement 氟烯酸A和B：含环戊烷抗氧化分子与酶触发的非酶骨架重排
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-19 DOI: 10.1021/acs.orglett.6c03809
Chunfang Yang,Xin Pang,Yuchan Chen,Wei Liu,Weilin Chen,Sinan Cao,Weimin Zhang,Changsheng Zhang,Wenjun Zhang
{"title":"Fluoindeneacids A and B: Antioxidant Cyclopentane-Containing Molecules with Enzyme-Triggered Nonenzymatic Skeletal Rearrangement","authors":"Chunfang Yang,Xin Pang,Yuchan Chen,Wei Liu,Weilin Chen,Sinan Cao,Weimin Zhang,Changsheng Zhang,Wenjun Zhang","doi":"10.1021/acs.orglett.6c03809","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03809","url":null,"abstract":"Fluoindeneacids A and B (5 and 6, respectively), featuring an unprecedented indene core linked to a 2,3-dihydroxybenzoyl moiety, were isolated from the FlsO1-catalyzed reaction of prejadomycin (1). Their structures were established by spectroscopic analysis and ECD calculations. Biochemical and isotopic labeling studies indicate their formation via an enzyme-triggered, nonenzymatic skeletal rearrangement of putative precursor 10. Both compounds exhibited potent in vitro antioxidant activity and cytoprotection against H2O2-induced damage.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"45 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218929","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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