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Synthesis, CrystallographicCharacterization, andProton-Modulated Physical Properties of an Azulene-Embedded ChiralNanographene azulene包埋手性纳米石墨烯的合成、晶体学表征和质子调制物理性质
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04215
Bihan Leng,Bing Li,Yiting Yang,Hang Ji,Hong Zhang,Sujuan Wang,Jinchong Xiao
{"title":"Synthesis, Crystallographic\u0000Characterization, and\u0000Proton-Modulated Physical Properties of an Azulene-Embedded Chiral\u0000Nanographene","authors":"Bihan Leng,Bing Li,Yiting Yang,Hang Ji,Hong Zhang,Sujuan Wang,Jinchong Xiao","doi":"10.1021/acs.orglett.6c04215","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04215","url":null,"abstract":"Abstract The construction of novel nanographenes embedded with non-benzenoid rings offers a promising platform for advanced optoelectronic applications. Postfunctionalization of the tribenzo[a,d,g]coronene scaffold with an azulene unit remains largely undeveloped. Herein, we rationally synthesized novel chiral azulene-modified nanographene 6, whose structure was unambiguously confirmed by single-crystal X-ray diffraction. Compound 6 bearing a [6]helicene subunit was resolved via chiral high-performance liquid chromatography (HPLC), and its enantiomers displayed mirror-image CD spectra in dichloromethane regardless of the presence or absence of trifluoroacetic acid. These findings advance the design of tribenzo[a,d,g]coronene-derived nanographenes with tunable optoelectronic properties.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209531","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 ofTrifluoromethylphosphines from Alkylphosphines 由烷基膦合成三氟甲基膦
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c03969
Yingfan Yang,Jinwei Zhang,Longhui Chen,Guangwei Wang,Hongtai Chen
{"title":"Synthesis of\u0000Trifluoromethylphosphines from Alkylphosphines","authors":"Yingfan Yang,Jinwei Zhang,Longhui Chen,Guangwei Wang,Hongtai Chen","doi":"10.1021/acs.orglett.6c03969","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03969","url":null,"abstract":"Abstract Despite their value as unique ligands, synthesizing trifluoromethylphosphines (TFMPhos) traditionally requires reactive precursors (bearing P–H, P–X, or P–Si bonds). Directly converting a P–C(sp3) into a P–CF3 bond remains a formidable challenge. Herein, we report a practical, transition-metal-free method for the direct conversion of alkylphosphines into TFMPhos using Togni’s reagent II and NaI. This operationally simple, mild protocol features broad functional group tolerance, providing versatile access to diverse TFMPhos derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209529","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
Water-ControlledDivergent Mechanochemical Synthesisof β-Keto Sulfones and Alkynyl Sulfones: A Unified Approach 水控分散机械化学合成β-酮砜和炔基砜：统一方法
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04170
Himanshu Chauhan,Anoop Sharma,Ajay Kumar Dhiya,Anuj Sharma
{"title":"Water-Controlled\u0000Divergent Mechanochemical Synthesis\u0000of β-Keto Sulfones and Alkynyl Sulfones: A Unified Approach","authors":"Himanshu Chauhan,Anoop Sharma,Ajay Kumar Dhiya,Anuj Sharma","doi":"10.1021/acs.orglett.6c04170","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04170","url":null,"abstract":"Abstract Herein, we report a water-controlled divergent mechanochemical sulfonylation of acetylenic carboxylic acids with sodium sulfinate salts. Under KI/TBHP-mediated ball-milling conditions, a low water content favors alkynyl sulfone formation, whereas excess water switches the reaction pathway to β-keto sulfones. The method accommodates aryl and alkyl sulfinate salts under transition-metal-, base-, and solvent-free conditions. Extension to α-methylstyrene substrates further demonstrates the broader applicability of this mechanochemical sulfonylation platform.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"230 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209522","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
Acid/Base-CatalyzedFunctional Group Metathesis Approachto Methoxy Group Isotopic Exchange of Aryl Methyl Ethers 芳基甲基醚甲氧基同位素交换的酸/碱催化官能团易位法
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04029
Bu-Hong Zhang,Tong Wang,Zengyu Zhang,Chen-Yuan Li,Xiaoyu Yan
{"title":"Acid/Base-Catalyzed\u0000Functional Group Metathesis Approach\u0000to Methoxy Group Isotopic Exchange of Aryl Methyl Ethers","authors":"Bu-Hong Zhang,Tong Wang,Zengyu Zhang,Chen-Yuan Li,Xiaoyu Yan","doi":"10.1021/acs.orglett.6c04029","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04029","url":null,"abstract":"Abstract We report a practical method for the direct isotopic exchange of methoxy groups in aryl methyl ethers using labeled methanol as an isotope source. A base-catalyzed system (t-BuOK/18-crown-6) is effective for electron-deficient substrates, whereas an acid-catalyzed system (MeOTf) is optimal for electron-rich substrates. Both protocols afforded deuterated products in high yields with excellent deuterium incorporation. The utility is demonstrated by labeling drug molecules and serving as an internal standard for HPLC–MS/MS analysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209530","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
ConformationallyRestricted GalN3 DonorsEnable Zinc(II)-Mediated Stereocontrolled Galactosylation 构象受限GalN3供体或可感知锌（II）介导的立体控制半乳糖基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c03888
Lan Ye,Guoqing Wang,Siai Zhou,Jiawei Li,Xiangtong Guo,Hui Cai,Feiqing Ding
{"title":"Conformationally\u0000Restricted GalN3 Donors\u0000Enable Zinc(II)-Mediated Stereocontrolled Galactosylation","authors":"Lan Ye,Guoqing Wang,Siai Zhou,Jiawei Li,Xiangtong Guo,Hui Cai,Feiqing Ding","doi":"10.1021/acs.orglett.6c03888","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03888","url":null,"abstract":"Abstract We report a Zn(II)-mediated stereocontrolled galactosylation with two conformationally restricted GalN3 donors that enables divergent α- and β-glycosylation. The 4,6-O-TIPDS/3-O-Bz donor selectively affords α-GalN3 glycosides, while the 4,6-O-benzylidene/3-O-TIPS donor provides β-glycosides with high stereoselectivity. The methods show a broad substrate scope, good yields, and scalability and enable synthesis of GalNAc-α-Ser and the Acinetobacter baumannii CPS K45 tetrasaccharide repeating unit.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"46 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209523","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
Tertiary AlkylHantzsch Nitriles as a Redox-NeutralPlatform for All-Carbon Quaternary Centers Construction via BimolecularHomolytic Substitution (SH2) 叔烷基汉氏腈作为双分子均解取代（SH2）构建全碳季中心的氧化还原中性平台
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04412
Yuxuan Wan,Yu Chen,Caiyun He,Tao Yang
{"title":"Tertiary Alkyl\u0000Hantzsch Nitriles as a Redox-Neutral\u0000Platform for All-Carbon Quaternary Centers Construction via Bimolecular\u0000Homolytic Substitution (SH2)","authors":"Yuxuan Wan,Yu Chen,Caiyun He,Tao Yang","doi":"10.1021/acs.orglett.6c04412","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04412","url":null,"abstract":"Abstract The construction of quaternary carbon centers remains an important yet challenging goal in synthetic chemistry. Herein, we report a photochemical nickel-mediated coupling of tertiary 4-alkyl Hantzsch nitriles derived from alkyl aldehydes with redox-active esters of primary carboxylic acids to forge sterically congested C(sp3)–C(sp3) bonds via SH2 under redox-neutral conditions. Two reaction protocols were established: one operates under 390 nm irradiation, whereas the other employs blue-light irradiation in the presence of an exogenous photocatalyst. These operationally simple protocols exhibit excellent functional group tolerance and provide general access to all-carbon quaternary centers from a previously unexplored substrate combination.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"63 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209524","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
[3+2] Cycloadditionsof Aldiminoboranes with N -Acylpyrazoles [3+2] aldinoboranes与N -酰基吡唑的环加成
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04005
Min Liu,Tongdao Wang
{"title":"[3+2] Cycloadditions\u0000of Aldiminoboranes with\u0000 N\u0000 -Acylpyrazoles","authors":"Min Liu,Tongdao Wang","doi":"10.1021/acs.orglett.6c04005","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04005","url":null,"abstract":"Abstract The [3+2] cycloaddition between aldiminoboranes and N-acylpyrazoles was successfully achieved. Aldiminoboranes, serving as C═N═B building blocks, were generated in situ via direct hydroboration of nitriles with Piers’ borane HB(C6F5)2. The [3+2] cycloaddition furnishes five-membered BN-heterocyclic compounds and notably features an acyl migration. Furthermore, the reaction exhibits a broad substrate scope with respect to both nitriles and N-acylpyrazoles, affording the target products in 56–87% isolated yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"64 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209528","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
Skeletal Modificationof Tryptophan Using Cyclic DiaryliodoniumSalts via Palladium-Catalyzed Cascade π-Extended AnnulativeDual C2–H/N–H Arylation 钯催化级联π扩展环双C2-H / N-H芳基化对环二芳基盐对色氨酸的骨架修饰
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c03837
Sowmya B. Udayakumar,Kiranmai Nayani
{"title":"Skeletal Modification\u0000of Tryptophan Using Cyclic Diaryliodonium\u0000Salts via Palladium-Catalyzed Cascade π-Extended Annulative\u0000Dual C2–H/N–H Arylation","authors":"Sowmya B. Udayakumar,Kiranmai Nayani","doi":"10.1021/acs.orglett.6c03837","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03837","url":null,"abstract":"Abstract We have demonstrated an efficient Pd-catalyzed annulative dual C2–H/N–H arylation reaction involving modification of the tryptophan indole skeleton to phenanthridinyl indole. This is an operationally simple and ligand-free strategy that was extended to biologically important indole derivatives and tryptophan-containing short peptides to deliver a diverse unnatural phenanthridinyl indole-tethered peptide with good efficiency. Notably, the method demonstrated good tolerance for N- and C-terminal protecting groups as well as for the side-chain functionalities of other amino acids.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"239 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209527","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
Criegee Intermediate-EnabledDecarboxylative C(sp3)–C(sp3) Cross-Couplingof α,β-UnsaturatedEsters with Cyclic Acetals α，β-不饱和酯与环缩醛交叉偶联的Criegee中间体激活脱羧C(sp3) -C (sp3
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03862
Soumya Mondal,Subal Mondal,Soumadeep Ghosh,Siba P. Midya,Iti Ghosh,Souvik Maiti,Pradyut Ghosh
{"title":"Criegee Intermediate-Enabled\u0000Decarboxylative C(sp3)–C(sp3) Cross-Coupling\u0000of α,β-Unsaturated\u0000Esters with Cyclic Acetals","authors":"Soumya Mondal,Subal Mondal,Soumadeep Ghosh,Siba P. Midya,Iti Ghosh,Souvik Maiti,Pradyut Ghosh","doi":"10.1021/acs.orglett.6c03862","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03862","url":null,"abstract":"Abstract Ozonolysis and Baeyer–Villiger (BV) rearrangement are among the earliest transformations in which cyclic/acyclic peroxo intermediates, often known as Criegee intermediates, have been detected. Herein, we disclose the merger of a Criegee intermediate with C(sp3)–C(sp3) cross-coupling via a rare anti-Giese addition for a new genre of C–C cross-coupling to access complex chemical libraries. Detailed mechanistic investigation reveals the generation of a cyclic tetrahedral peroxo intermediate (CI), and gas-phase analysis establishes the formation of 16O═C═18O under 18O2 conditions and straightforwardly supports the formation of peroxylactones via a Criegee intermediate under our standard conditions. Importantly, many pharmaceutically active drug-like molecules have been screened thoroughly and have been shown to exhibit excellent tolerance and high regioselectivity for this methodology.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209559","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
Bicyclic BODIPY-SubmonoazaporphyrinHybrids via aCatalyst-Free SNAr Strategy: Coexisting Local Aromaticityand Global Antiaromaticity with Broad NIR-II Absorption 通过无催化剂SNAr策略的双环bodipy -亚单氮卟啉杂合体：具有广泛NIR-II吸收的局部芳香性和全局抗芳香性共存
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03941
Yingjian Shang,Zhongxin Li,Haolin He,Wenxin Gu,Sihan Zheng,Huiquan Zuo,Yaxiong Wei,Erhong Hao,Lijuan Jiao
{"title":"Bicyclic BODIPY-Submonoazaporphyrin\u0000Hybrids via a\u0000Catalyst-Free SNAr Strategy: Coexisting Local Aromaticity\u0000and Global Antiaromaticity with Broad NIR-II Absorption","authors":"Yingjian Shang,Zhongxin Li,Haolin He,Wenxin Gu,Sihan Zheng,Huiquan Zuo,Yaxiong Wei,Erhong Hao,Lijuan Jiao","doi":"10.1021/acs.orglett.6c03941","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03941","url":null,"abstract":"Abstract A series of bicyclic BODIPY-submonoazaporphyrin hybrids were efficiently constructed via a catalyst-free SNAr strategy, exhibiting excellent chemical stability. These hybrids exhibit a unique coexistence of local 14π aromaticity and global 28π antiaromaticity, which was unambiguously verified by NMR spectroscopy and theoretical calculations. Moreover, they show remarkably broad UV–vis–NIR absorption spanning the range of 300–1400 nm (NIR-II) and rich redox properties, thereby providing an effective strategy for designing novel porphyrinoids with tunable aromaticity as stable NIR functional materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209563","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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