Organic Chemistry Frontiers最新文献_第4页

Pyridyl Phosphonium Salts: A Comprehensive Account of Their Preparation, Reactivity, and Synthetic Applications 吡啶基磷酸盐：它们的制备、反应性和合成应用的综合叙述

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01118g

Eklakh Ansari,Manish Kumar Sharma,Anand Ratnam,Nazar Hussain

{"title":"Pyridyl Phosphonium Salts: A Comprehensive Account of Their Preparation, Reactivity, and Synthetic Applications","authors":"Eklakh Ansari,Manish Kumar Sharma,Anand Ratnam,Nazar Hussain","doi":"10.1039/d6qo01118g","DOIUrl":"https://doi.org/10.1039/d6qo01118g","url":null,"abstract":"Pyridyl phosphonium salts have emerged as a versatile class of synthetic reagents for the regioselective C4 functionalization of pyridines and related N-heteroarenes, providing an effective platform for the modification of electron-deficient azaarenes. These salts can be readily prepared as stable, free-flowing solids and isolated without the need for chromatographic purifications. Moreover, such reagents showed excellent air and thermal stability and enable the construction of diverse C-C and C-heteroatom bonds under mild reaction conditions. Since the pioneering work reported in 2016, the synthetic utility of pyridyl phosphonium salts has expanded considerably to encompass cross-coupling, pyridine-pyridine coupling, photocatalytic transformations, carboxylation, sulfonylation, halogenation, alkylation, fluoroalkylation, amination, hydrogen isotope exchange, and other valuable transformations. To the best of our knowledge, this review represents the first comprehensive account dedicated exclusively to pyridyl phosphonium salts, covering their preparation, reactivity, and synthetic applications. Particular emphasis is placed on reaction scope, substrate compatibility, mechanistic insights, and the advantages and limitations of the reported methodologies. Representative applications in late-stage functionalization are highlighted, together with current challenges and future perspectives for the continued development of pyridyl phosphonium salt chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151938","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

Micellar Iron Catalysis for Aromatic C–H Hydroxylation 胶束铁催化芳香族C-H羟基化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01366j

Raj Sunil Wandre,Maryam Nabi,Kirti Sharma,Amol B. Gade

引用次数: 0

Synthesis of azulene fluorophores reveals structure–property relationships azulene荧光团的合成揭示了结构-性质关系

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01099g

Chiara Faverio,João Gabriel Ribeiro,Mehmet Kaplan,Gabriele Kociok-Köhn,Tony D. James,G. Dan Pantoş,Simon E. Lewis

引用次数: 0

Diastereoselective TMSOTf-mediated alkyne-Prins cyclisation to access mono- and bicyclic Δ-vinyltriflated disubstituted -2,7-oxepenes 非对映选择性tmsotf介导的炔-普林斯环化以获得单环和双环Δ-vinyltriflated二取代-2,7-氧烯

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-28 DOI: 10.1039/d6qo01120a

Davide Andrea Coppini,Victoria Sinka,Carla Alamillo-Ferrer,Israel Fernández,Jordi Burés,Juan I. Padrón

引用次数: 0

Heating-induced cascade annulation of CF 3 -imidoyl sulfoxonium ylides with thioamides for the synthesis of multi-substituted imidazolines via sulfur and acyl migration 通过硫和酰基迁移，热诱导的cf3 -咪甲酰亚砜酰化与硫酰胺的级联环合成多取代咪唑啉

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-28 DOI: 10.1039/d6qo01167e

Zhenwei Yu,Yu Zhang,Zhengkai Chen

引用次数: 0

Visible-light-driven radical difluoroalkylation/cyclization of N-allyl and N-homoallyl aldehyde hydrazones with [Ph3PCF2H]+Br 与[Ph3PCF2H]+Br的n -烯丙基和n -均烯丙醛腙的可见光驱动自由基二氟烷基化/环化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-28 DOI: 10.1039/d6qo01138a

Jin-Kui Chai,Li-Li Wang,Shi-Long Zhang,Xiao-Xiao Zhu,Jin-Wei Yuan,Yong-Mei Xiao,Shouren Zhang,Lingbo Qu

引用次数: 0

Remote and Site-Selective C–H Functionalization of Benzamides Enabled by Palladium 1,7-Migration 钯1,7迁移使苯酰胺类化合物的C-H远程选择性官能化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-28 DOI: 10.1039/d6qo00906a

Norman Le Floch,Thierry Roisnel,Henri Doucet

{"title":"Remote and Site-Selective C–H Functionalization of Benzamides Enabled by Palladium 1,7-Migration","authors":"Norman Le Floch,Thierry Roisnel,Henri Doucet","doi":"10.1039/d6qo00906a","DOIUrl":"https://doi.org/10.1039/d6qo00906a","url":null,"abstract":"Palladium migration represents an attractive strategy for the functionalization of otherwise difficult-to-activate C–H bonds. Among these processes, Pd 1,4-migration was the most extensively studied, although examples of 1,2-, 1,3-, and 1,5-migrations have also been reported. In contrast, Pd 1,7-migration enabling the functionalization of distal C–H bonds remains exceedingly rare. The functionalization of specific C-H bonds of (hetero)arenes is a topic currently receiving significant attention, as it may enable the preparation of complex molecules in fewer steps. Herein, we report that N-(2-bromobenzyl)carboxamides bearing (hetero)aryl substituents on the amide undergo selective heteroarylation at the benzamide ring, rather than at the benzyl moiety, in the presence of heteroarenes and a palladium catalyst. Mechanistic investigations suggest that this transformation proceeds through an unusual Pd 1,7-migration, enabling C–C bond formation via dual C–H bond functionalization, while the bromobenzyl substituent behaves as a traceless directing group. The method tolerates a broad range of heteroarenes and benzamide derivatives. This strategy provides a synthetically valuable and regioselective approach to the heteroarylation of benzamides, particularly because the preparation of ortho-brominated benzamide substrates is often challenging.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"219 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149067424","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-driven electron donor-acceptor complex induced C-H functionalization of 2-arylindoles with α-Br ketones 可见光驱动的电子供体-受体配合物诱导2-芳酮与α-溴酮的碳氢功能化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-28 DOI: 10.1039/d6qo01260d

Baoheng Wu,Tao Chen,Dengshan Pan,Tianyi Liu,Jinglin Liu,Jiuming Li,Ning Xu,Hua Xiao,Liang Xu,Xinxin Jin,Wei-Lei Zhou,He Li

引用次数: 0

Solvent Controlled Palladium-Catalyzed β-Regioselective Hydroamination of Allenoates with Azole Heterocycles 溶剂控制钯催化的含唑杂环烯丙酸酯的β-区域选择性胺化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-23 DOI: 10.1039/d6qo01177b

Kaixuan Pan,Xin Bai,Wanshu Wang,Lu Gao,Zhenlei Song,Xiaoxiao Tang

引用次数: 0

Deciphering Competing Reaction Pathways in the α-C-H Functionalization of Unprotected Alicyclic Amines via Ketone-Mediated Hydride Transfer 通过酮介导的氢化物转移解读无保护脂环胺α-C-H功能化的竞争反应途径

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-09-23 DOI: 10.1039/d6qo01213b

Daniel Valles,Saikat Das,Subhrashis Banerjee,Subhradeep Dutta,Weijie Chen,Martin Breugst,Mathew J. Vetticatt,Daniel Seidel

{"title":"Deciphering Competing Reaction Pathways in the α-C-H Functionalization of Unprotected Alicyclic Amines via Ketone-Mediated Hydride Transfer","authors":"Daniel Valles,Saikat Das,Subhrashis Banerjee,Subhradeep Dutta,Weijie Chen,Martin Breugst,Mathew J. Vetticatt,Daniel Seidel","doi":"10.1039/d6qo01213b","DOIUrl":"https://doi.org/10.1039/d6qo01213b","url":null,"abstract":"Alicyclic amines are pervasive in pharmaceuticals and natural products, yet direct α-C-H functionalization of unprotected secondary amines remains a long-standing challenge. Building on the historical oxidation of lithium amides by ketones, we present a combined experimental and computational study that establishes the mechanistic basis for α-functionalization of these substrates. Competition experiments, ReactIR monitoring, kinetic isotope effects, and DFT calculations demonstrate that imine formation proceeds through concerted hydride transfer from solvent-coordinated monomeric lithium amides. Nucleophilic addition of lithium amides to the ketone oxidant is identified as a major yield-limiting side reaction and is shown to depend strongly on amine ring size, oxidant electrophilicity, and steric effects. Regioselectivity in α-substituted amines arises from a combination of steric and electronic factors governing C-H bond activation. These findings clarify the fundamental reactivity of lithium amides and provide a practical platform for the synthesis of polysubstituted alicyclic amines without protecting groups or transition metals.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"36 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149013646","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