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Metal-free aerobic epoxidation of aromatic olefins using V-70 and pivalaldehyde 用V-70和戊醛进行芳香烯烃无金属有氧环氧化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-02 DOI: 10.1016/j.tetlet.2025.155878
Yamato Kato, Miho Kanoh, Hazuki Itoh, Shiori Itoh, Sakura Tanaka, Takayuki Shioiri, Masato Matsugi
{"title":"Metal-free aerobic epoxidation of aromatic olefins using V-70 and pivalaldehyde","authors":"Yamato Kato,&nbsp;Miho Kanoh,&nbsp;Hazuki Itoh,&nbsp;Shiori Itoh,&nbsp;Sakura Tanaka,&nbsp;Takayuki Shioiri,&nbsp;Masato Matsugi","doi":"10.1016/j.tetlet.2025.155878","DOIUrl":"10.1016/j.tetlet.2025.155878","url":null,"abstract":"<div><div>A metal-free aerobic epoxidation of olefins was achieved using V-70 (2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile)) as a low-temperature radical initiator in combination with pivalaldehyde as a co-oxidant. The method operates under mild conditions with air as the oxidant, converting a broad range of olefins to epoxides in good to excellent yields. This protocol avoids hazardous peroxides, high-valent metal reagents, and halogenated solvents, offering an environmentally benign and practical approach to olefin epoxidation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155878"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145463894","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Examining the silicon‑fluorine gauche effect in 3-fluoro silacyclohexanes 3-氟硅环己烷中硅氟间扭扭效应的研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-20 DOI: 10.1016/j.tetlet.2025.155902
K.E. Wier, S.M. Conner, R.F. Berger, G.W. O'Neil
{"title":"Examining the silicon‑fluorine gauche effect in 3-fluoro silacyclohexanes","authors":"K.E. Wier,&nbsp;S.M. Conner,&nbsp;R.F. Berger,&nbsp;G.W. O'Neil","doi":"10.1016/j.tetlet.2025.155902","DOIUrl":"10.1016/j.tetlet.2025.155902","url":null,"abstract":"<div><div>Two 3-fluorosilinanes featuring different substitution at silicon were synthesized and their conformations analyzed by NMR and DFT. Based on the results, both compounds prefer a conformation wherein the fluorine atom is oriented equatorial rather than axial, which would have placed the partially negative fluorine (F<sup>δ-</sup>) closer in space to partially positive silicon (Si<sup>δ+</sup>). Therefore, the conformational preference of these systems is thought to be controlled primarily by sterics as well as hyperconjugative stabilization (σ<sub>C-Si</sub> → σ*<sub>C-F</sub>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155902"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576484","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Efficient cyanation of amides and thioamides via difluorocarbene-mediated dehydration and desulfurization 通过二氟烃介导的脱水和脱硫高效氰化酰胺和硫酰胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-07 DOI: 10.1016/j.tetlet.2025.155891
Tao Zhao, Zixin Chen, Jinghan Bu, Mengyi Huang, Qiang Yang
{"title":"Efficient cyanation of amides and thioamides via difluorocarbene-mediated dehydration and desulfurization","authors":"Tao Zhao,&nbsp;Zixin Chen,&nbsp;Jinghan Bu,&nbsp;Mengyi Huang,&nbsp;Qiang Yang","doi":"10.1016/j.tetlet.2025.155891","DOIUrl":"10.1016/j.tetlet.2025.155891","url":null,"abstract":"<div><div>A novel method involving difluorocarbene-mediated dehydration and desulfurization-cyanation of amides and thioamides has been developed. This approach facilitates the efficient conversion of diverse substrates—including alkyl, alkenyl, alkynyl, and aryl amides, as well as thioamides, urea, and amino acid derivatives—under transition-metal-free conditions without an inert atmosphere. Notably, this strategy provides a straightforward protocol for the late-stage cyanation modification of pharmaceutical amides and other bioactive molecules. The procedure is operationally simple, and some products require only extraction and purification, eliminating the need for column chromatography.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155891"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145525924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 highly regioselective hydroarylation of 1, 3-dienes with phenyl formates 钯催化的1,3 -二烯与甲酸苯酯的高度区域选择性氢化芳基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-11 DOI: 10.1016/j.tetlet.2025.155879
Teng Xu, Xin-Yi Hou, Yong-Chao Sun, Sheng Wang, Ao-Yu Li, Shan-Shan Chen
{"title":"Palladium-catalyzed highly regioselective hydroarylation of 1, 3-dienes with phenyl formates","authors":"Teng Xu,&nbsp;Xin-Yi Hou,&nbsp;Yong-Chao Sun,&nbsp;Sheng Wang,&nbsp;Ao-Yu Li,&nbsp;Shan-Shan Chen","doi":"10.1016/j.tetlet.2025.155879","DOIUrl":"10.1016/j.tetlet.2025.155879","url":null,"abstract":"<div><div>This work developed a palladium-catalyzed <em>ortho</em>-selective allylic alkylation reaction using phenol derivatives and 1, 3-dienes to synthesize allyl phenolic compounds. A range of 1, 3-dienes and aryl formates were successfully coupled, achieving moderate to good yields with excellent site-selectivity for the allylic products. Additionally, gram-scale reactions demonstrated process's scalability, while chiral ligands facilitated the production of chiral allyl phenols with notable enatiomeric excess. Through derivation studies, further transformations were explored, highlighting the versatility and potential applications of this methodology in synthetic organic chemistry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155879"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145525926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Efficient synthesis of aryl sulfonyl fluorides via an economical reductive fluorosulfonation strategy under mild conditions 在温和条件下通过经济的还原性氟磺化策略高效合成芳基磺酰氟
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-22 DOI: 10.1016/j.tetlet.2025.155865
Sangni Jiang , Zhihui Lu
{"title":"Efficient synthesis of aryl sulfonyl fluorides via an economical reductive fluorosulfonation strategy under mild conditions","authors":"Sangni Jiang ,&nbsp;Zhihui Lu","doi":"10.1016/j.tetlet.2025.155865","DOIUrl":"10.1016/j.tetlet.2025.155865","url":null,"abstract":"<div><div>This study presents a novel and cost-effective method for synthesizing aryl sulfonyl fluorides using economically accessible starting materials, including the Et<sub>3</sub>N·HF complex as a safe HF surrogate. Upon reaction with SO<sub>2</sub>, this reagent generates the fluorosulfonating reagent triethylamine fluorosulfinate (FSO<sub>2</sub><sup>−</sup>Et<sub>3</sub>NH<sup>+</sup>) in-situ<sub>.</sub> Acting as both a reducing agent and a reactive intermediate, it enables efficient reactions with aromatic diazonium salts at room temperature without requiring additional oxidants. The approach facilitates the synthesis of diverse aryl sulfonyl fluorides in high yields, addressing limitations of prior methods that often rely on costly reagents or catalysts.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155865"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361384","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Transition metal free functionalization of nitrogen heterocycles, triggered and driven by electrophilic acetylenes 亲电乙炔引发和驱动的氮杂环过渡金属游离功能化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-12-15 Epub Date: 2025-09-23 DOI: 10.1016/j.tetlet.2025.155837
Boris A. Trofimov, Kseniya V. Belyaeva
{"title":"Transition metal free functionalization of nitrogen heterocycles, triggered and driven by electrophilic acetylenes","authors":"Boris A. Trofimov,&nbsp;Kseniya V. Belyaeva","doi":"10.1016/j.tetlet.2025.155837","DOIUrl":"10.1016/j.tetlet.2025.155837","url":null,"abstract":"<div><div>The review covers the advances reached during the last five years in transition metal free functionalization and modification of nitrogen heterocycles with electrophilic acetylenes. The reactions are triggered and further driven by the initially formed 1,3(4)-dipole complexes (zwitterions), adducts of the nucleophilic attack of nitrogen heterocycles at the triple electrophilic carbon‑carbon bond of the acetylenes. The carbanionic sites of these zwitterions are usually captured by electrophiles such as second molecule of the acetylenes or other electrophilic C<img>C and C<img>O unsaturated compounds, as well as various CH<img>, OH<img>, NH<img>, PH<img> acids thereby raising molecular complexity (in the course of diverse cascade transformations) to a new higher level. The rich energy potential of the activated carbon‑carbon triple bond warrants mild reaction conditions and allows the functionalization to be performed without transition metal catalysts.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155837"},"PeriodicalIF":1.5,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145218393","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Ir-catalyzed distal branch- and enantioselective hydroarylation of internal alkenes using acetanilides via chain-walking and CH activation 通过链走和CH活化，用乙酰苯胺催化远端分支和对映选择性内烯烃氢化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-12-15 Epub Date: 2025-09-10 DOI: 10.1016/j.tetlet.2025.155823
Mizuki Kadota, King Hung Nigel Tang, Takanori Shibata
{"title":"Ir-catalyzed distal branch- and enantioselective hydroarylation of internal alkenes using acetanilides via chain-walking and CH activation","authors":"Mizuki Kadota,&nbsp;King Hung Nigel Tang,&nbsp;Takanori Shibata","doi":"10.1016/j.tetlet.2025.155823","DOIUrl":"10.1016/j.tetlet.2025.155823","url":null,"abstract":"<div><div>This study presents the iridium-catalyzed branch- and enantioselective C<img>H alkylation of acetanilides with internal alkenes via chain-walking. This report addresses a key challenge in the selective C<img>C bond formation by using a newly developed electron-deficient TADDOL-based chiral ligand and we achieved an optimal balance between yield and enantiomeric ratio (up to 91:9 er). The use of 1.5 equivalent amounts of [Ir(cod)<sub>2</sub>]NTf<sub>2</sub> relative to chiral ligands significantly improved the yields along with perfect regioselectivity and good enantioselectivity. The substrate scope demonstrated the broad applicability of the method across various acetanilide and alkene derivatives, including functionalized arenes and alkenes bearing aryl or aliphatic substituents.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155823"},"PeriodicalIF":1.5,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145157010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Silver-catalyzed regioselective synthesis of benzo[2,7] naphthyridines using ortho-alkynyl quinoline carbaldehyde and anthranilic acid derivatives 银催化邻炔基喹啉乙醛和邻氨基苯甲酸衍生物的区域选择性合成苯并[2,7]萘啶
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-12-15 Epub Date: 2025-09-20 DOI: 10.1016/j.tetlet.2025.155835
Kapil Chahal , Ravikumar Badhavath , K. Velangini Sunidhi Reddy , Kirti Vashishtha , K. Rajender Reddy
{"title":"Silver-catalyzed regioselective synthesis of benzo[2,7] naphthyridines using ortho-alkynyl quinoline carbaldehyde and anthranilic acid derivatives","authors":"Kapil Chahal ,&nbsp;Ravikumar Badhavath ,&nbsp;K. Velangini Sunidhi Reddy ,&nbsp;Kirti Vashishtha ,&nbsp;K. Rajender Reddy","doi":"10.1016/j.tetlet.2025.155835","DOIUrl":"10.1016/j.tetlet.2025.155835","url":null,"abstract":"<div><div>This method represents a significant advancement in the synthesis of Benzo[2,7]naphthyridines. The silver-catalyzed cyclization of <em>ortho</em>-alkynyl aldehydes and anthranilic acids proceeds under mild conditions with minimal catalyst loading, providing high yields and excellent regioselectivity. Control experiments and deuteration studies were performed to evaluate the reaction mechanism. The broad substrate scope and scalability make this protocol especially valuable for synthesizing diverse 2,7-naphthyridine derivatives, which are important scaffolds in medicinal chemistry and materials science.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155835"},"PeriodicalIF":1.5,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145128258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 phosphonium ylidyl-carbonylation of aryl bromides for the synthesis of α-acylphosphoranes 钯催化芳基溴基乙烯基羰基化合成α-酰基磷烷
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-12-15 Epub Date: 2025-10-08 DOI: 10.1016/j.tetlet.2025.155849
Xiao-Jun Guo , Rong-Xin Fan , Tian-Tian Wang , Qiu-Ya Wang , Xiu-Qin Cai , Bo Liu , Xiao-Qiang Zhou
{"title":"Palladium-catalyzed phosphonium ylidyl-carbonylation of aryl bromides for the synthesis of α-acylphosphoranes","authors":"Xiao-Jun Guo ,&nbsp;Rong-Xin Fan ,&nbsp;Tian-Tian Wang ,&nbsp;Qiu-Ya Wang ,&nbsp;Xiu-Qin Cai ,&nbsp;Bo Liu ,&nbsp;Xiao-Qiang Zhou","doi":"10.1016/j.tetlet.2025.155849","DOIUrl":"10.1016/j.tetlet.2025.155849","url":null,"abstract":"<div><div>We report a palladium-catalyzed carbonylation protocol for the synthesis of α-acylphosphoranes using low-cost aryl bromides and stabilized phosphonium ylides under 1 atm of carbon monoxide (CO). A broad range of α-acylphosphoranes can be obtained in moderate to excellent yields with good functional group tolerance under mild reaction conditions, showcasing the potential of the method in synthetic organic chemistry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155849"},"PeriodicalIF":1.5,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145321789","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Tandem Mizoroki-Heck arylation and Aza-Michael reaction: A rapid access to 1,3-Disubstituted-1,2-dihydroisoquinoline derivatives 串联Mizoroki-Heck芳基化和Aza-Michael反应：快速获得1,3-二取代-1,2-二氢异喹啉衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-12-15 Epub Date: 2025-10-06 DOI: 10.1016/j.tetlet.2025.155844
Manisha Kundu, Rajat Ghosh, Shital K. Chattopadhyay
{"title":"Tandem Mizoroki-Heck arylation and Aza-Michael reaction: A rapid access to 1,3-Disubstituted-1,2-dihydroisoquinoline derivatives","authors":"Manisha Kundu,&nbsp;Rajat Ghosh,&nbsp;Shital K. Chattopadhyay","doi":"10.1016/j.tetlet.2025.155844","DOIUrl":"10.1016/j.tetlet.2025.155844","url":null,"abstract":"<div><div>A one-pot Pd-catalyzed Larock-type [3 + 3]-annulation of an 2-iodoarene with 2-amidoacrylates has been developed which provides an easy access to 1,3-disubstituted-1,2-dihydroisoquinoline derivatives in good yields (54–71 %). The process involves Mizoroki-Heck type arylation as the first step followed by spontaneous intramolecular aza-Michael reaction mediated ring closure.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155844"},"PeriodicalIF":1.5,"publicationDate":"2025-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145264130","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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