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1,4-Bis(aryl)-[1,2,4,5]-tetrazines prepared by light-driven ring-expansion skeletal editing 光驱动扩环骨架编辑制备1,4-双（芳基）-[1,2,4,5]-四嗪类化合物
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-04-28 DOI: 10.1039/d6qo00275g
Yu Xin, Jinsong Jiang, Junyuan Zhao, Yihang Suo, Hongwei Hou, Xiuwen Zhou, Jie Ding
{"title":"1,4-Bis(aryl)-[1,2,4,5]-tetrazines prepared by light-driven ring-expansion skeletal editing","authors":"Yu Xin,&nbsp;Jinsong Jiang,&nbsp;Junyuan Zhao,&nbsp;Yihang Suo,&nbsp;Hongwei Hou,&nbsp;Xiuwen Zhou,&nbsp;Jie Ding","doi":"10.1039/d6qo00275g","DOIUrl":"10.1039/d6qo00275g","url":null,"abstract":"<div><div>Nitrogen-containing heterocycles are essential components in the medicine–agriculture–materials continuum and beyond. Recently, functional N-heterocycles have been facilely prepared by light-driven skeletal editing, starting with easily accessible compounds. In this work, three 1,4-bis(aryl)-1,2,4,5-tetrazine compounds, (<em>n</em> = 1, 2, 3), which were difficult to attain <em>via</em> previously reported synthetic strategies, were successfully synthesized through light-driven ring-expansion skeletal editing of 2,5-disubstituted tetrazoles. Spectroscopic analyses and density functional theory (DFT/TD-DFT) calculations confirmed that the unique multiple emission of in solution and powdered forms exhibits anti-Kasha-like characteristics. Additionally, the compact, twisted π-systems based on a tetrazine core demonstrated attractive cubic nonlinear optical (NLO) capabilities.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 3960-3968"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147755316","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Modular multicomponent cascade synthesis of benzo[b]thiophene-fused N,O-heterocycles from 1,2-benzisothiazoles, benzolactones and aldehydes 1,2-苯并异噻唑、苯并内酯和醛的模块化多组分级联合成苯并[b]噻吩- N， o杂环
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-05-14 DOI: 10.1039/d6qo00413j
Longzhi Lin, Jie Ren, Heying Chen, Shuang Liu, Chuanjun Song, Junbiao Chang, Yangang Wu
{"title":"Modular multicomponent cascade synthesis of benzo[b]thiophene-fused N,O-heterocycles from 1,2-benzisothiazoles, benzolactones and aldehydes","authors":"Longzhi Lin,&nbsp;Jie Ren,&nbsp;Heying Chen,&nbsp;Shuang Liu,&nbsp;Chuanjun Song,&nbsp;Junbiao Chang,&nbsp;Yangang Wu","doi":"10.1039/d6qo00413j","DOIUrl":"10.1039/d6qo00413j","url":null,"abstract":"<div><div>A modular, metal-free multicomponent cascade reaction for the synthesis of benzo[<em>b</em>]thiophene-fused seven- or eight-membered N,O-heterocyclic compounds from 1,2-benzisothiazoles, benzolactones, and aldehydes has been developed. Notably, 1,2-benzisothiazoles were employed as novel sulfuration reagents in multicomponent reactions for the first time. The regioselectivity of this modular transformation is controlled by the <em>in situ</em> ring-opening of 1,2-benzisothiazoles with benzolactones, a process involving N–S bond cleavage and decarboxylation. This modular multicomponent cascade reaction proceeds under mild conditions, exhibits broad substrate tolerance, and enables the one-step formation of new C–C, C–S, C–N, and C–O bonds. Moreover, the successful scale-up synthesis and efficient late-stage modification of pharmaceutical molecules highlight the synthetic utility of this method.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 4095-4101"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148503288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A generalized electrochemical dehydrogenation approach en route to α-phosphorylated amines α-磷酸化胺的通用电化学脱氢方法
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-05-14 DOI: 10.1039/d6qo00588h
Nayan Saha, Shana Chandran, Burkhard König
{"title":"A generalized electrochemical dehydrogenation approach en route to α-phosphorylated amines","authors":"Nayan Saha,&nbsp;Shana Chandran,&nbsp;Burkhard König","doi":"10.1039/d6qo00588h","DOIUrl":"10.1039/d6qo00588h","url":null,"abstract":"<div><div>Given the widespread use of organophosphorus scaffolds in several disciplines, the formation of C(sp<sup>3</sup>)–P bonds is of fundamental importance. Direct access to α-phosphorylated amines still remains challenging, though, because conventional methods frequently call for substrate-specific photocatalytic conditions, stoichiometric oxidants, or prefunctionalized substrates. Here, we provide a broad electrochemical approach for the direct phosphorylation of feedstock amines and peptides. Under ambient conditions, the reaction proceeds <em>via</em> anodic oxidation, producing an α-amino radical and cationic intermediates that are efficiently coupled with secondary phosphine oxide-, phosphonate-, and phosphinate-based nucleophiles. Overall, this platform's redox-neutral characteristics, broad substrate range, functional group tolerance, and scalability enable the efficient synthesis of a variety of α-phosphorylated amines. A generic and sustainable solution for C–P bond formation is provided by incorporating electrochemical activation into organophosphorus chemistry, opening new possibilities for the creation of organophosphorus ligands and bioactive compounds.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 4052-4063"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148503396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Breaking C–C (sp3–sp3) σ bonds in 1,4-diazabicyclo[2.2.2]octane (DABCO) by oxidation with antimony pentachloride 五氯化锑氧化破坏1,4-重氮杂环[2.2.2]辛烷（DABCO）中C-C (sp 3 -sp 3) σ键
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-04-13 DOI: 10.1039/d5qo01513h
Lilia M. Baldauf, David G. Villarreal, Guodong Rao, Nathan Yoshino, Heejune Park, James C. Fettinger, Lee-Ping Wang, R. David Britt, Alan L. Balch
{"title":"Breaking C–C (sp3–sp3) σ bonds in 1,4-diazabicyclo[2.2.2]octane (DABCO) by oxidation with antimony pentachloride","authors":"Lilia M. Baldauf,&nbsp;David G. Villarreal,&nbsp;Guodong Rao,&nbsp;Nathan Yoshino,&nbsp;Heejune Park,&nbsp;James C. Fettinger,&nbsp;Lee-Ping Wang,&nbsp;R. David Britt,&nbsp;Alan L. Balch","doi":"10.1039/d5qo01513h","DOIUrl":"10.1039/d5qo01513h","url":null,"abstract":"<div><div>Evidence for the oxidative cleavage of the C–C (sp<sup>3</sup>–sp<sup>3</sup>) σ bond of DABCO (1,4-diazabicyclo[2.2.2]octane) is reported. Two crystalline salts have been characterized by XRD analysis, which provides insight into the possible mechanism of bond scission that occurred. EPR and ENDOR spectra of the reaction solutions show the existence of two radical species: the delocalized DABCO˙<sup>+</sup> cation, where the electron is delocalized between the two nitrogen nuclei, and a localized DABCO˙<sup>+</sup> radical cation with two different hyperfine couplings to the two nitrogen atoms. Computations suggest that the latter radical is DABCO˙<sup>+</sup> complexed with SbCl<sub>5</sub>. DFT and mechanistic analysis provides possible mechanisms for the C–C bond scission, including a newly proposed intermediate: the methylenevinylpiperazine (MVP) radical cation.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 3888-3899"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147664513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantioselective synthesis of tetrahydrofurans by permanganate-mediated oxidative cyclisation of 1,5-dienes using chiral phase-transfer catalysis 用手性相转移催化高锰酸盐介导1,5-二烯氧化环化对映选择性合成四氢呋喃
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-05-19 DOI: 10.1039/d6qo00377j
Nikita S. Rank, Aqeel A. Hussein, Alexander L. Cecil, Mark E. Light, Richard C. D. Brown
{"title":"Enantioselective synthesis of tetrahydrofurans by permanganate-mediated oxidative cyclisation of 1,5-dienes using chiral phase-transfer catalysis","authors":"Nikita S. Rank,&nbsp;Aqeel A. Hussein,&nbsp;Alexander L. Cecil,&nbsp;Mark E. Light,&nbsp;Richard C. D. Brown","doi":"10.1039/d6qo00377j","DOIUrl":"10.1039/d6qo00377j","url":null,"abstract":"<div><div>Permanganate-mediated oxidative cyclisation of 1,5-dienes under chiral phase transfer catalysis (CPTC) conditions provides 2,5-dihydroxyalkyl substituted tetrahydrofurans (THF-diols) wherein four new C–O bonds are established with excellent control of relative and absolute stereochemistry. Structurally complex THF-containing motifs found in a host of bioactive natural products are accessible by oxidative transformation of simple dienes, which is exemplified by formal syntheses of <em>cis</em>-solamin A. Electron-withdrawing ester or ketone groups in the substrates – conjugated to one alkene of the 1,5-diene system – direct the initial manganation reaction to the electron-deficient alkene, which proceeds with enantiofacial selectivity in the presence of the CPTC. Cinchona alkaloid scaffolds are a convenient platform for chiral quaternary ammoniums with short synthetic routes to anthracenylmethyl and 3,5-bis(trifluoromethylbenzyl) CPTC derivatives realising enantioselectivities up to 89–94% ee for structurally distinct 1,5-diene systems using a readily-available and inexpensive oxidant. DFT calculations provide significant new mechanistic insight into the permanganate-mediated reaction supporting the involvement of a protonated Mn(<span>v</span>) glycolate in THF ring-formation through enhanced electrophilicity of the metal oxo intermediate. Furthermore, calculations identify the interplay between dipole-driven electrostatic stabilisation and cooperative noncovalent interactions in the transition state complex for manganation in the first reaction step, leading to the observed facial selectivity in this powerful synthetic reaction.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 4078-4088"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148503377","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Copper-catalyzed three-component spiroannulation: modular access to 1,3,7,8-tetraazaspiro[4.4]nona-3,6-dienes via a metal-free and subsequent Cu(ii) relay strategy 铜催化的三组分螺旋环：通过无金属和随后的Cu（ii）接力策略模块化获取1,3,7,8-四氮杂螺[4.4]-3,6-二烯
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-05-12 DOI: 10.1039/d6qo00309e
Dong-Fang Jiang, Hao Dong, Yutong Tang, Jia Zhou, Xin Xiong, Min Tang, Zhenjie Qi, Wei-Min He
{"title":"Copper-catalyzed three-component spiroannulation: modular access to 1,3,7,8-tetraazaspiro[4.4]nona-3,6-dienes via a metal-free and subsequent Cu(ii) relay strategy","authors":"Dong-Fang Jiang,&nbsp;Hao Dong,&nbsp;Yutong Tang,&nbsp;Jia Zhou,&nbsp;Xin Xiong,&nbsp;Min Tang,&nbsp;Zhenjie Qi,&nbsp;Wei-Min He","doi":"10.1039/d6qo00309e","DOIUrl":"10.1039/d6qo00309e","url":null,"abstract":"<div><div>A continuous one-pot protocol involving a metal-free oxidative 5-<em>exo-trig</em> cyclization of β,γ-unsaturated hydrazones, followed by Cu(<span>ii</span>)-catalyzed intermolecular [3 + 2] cycloaddition with oximes and nitriles, has been established. Over 90 examples of 1,3,7,8-tetraazaspiro[4.4]nona-3,6-dienes were obtained <em>via</em> this spirocyclization under air. This protocol features excellent functional group tolerance, and a wide range of aryl, heteroaryl, alkyl, ketone, ester, ether, thiol ether, silane, alkene, allene, and alkyne groups are all well tolerated.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 13","pages":"Pages 3909-3914"},"PeriodicalIF":0.0,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148503388","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A photoswitchable macrocyclic ion-pair receptor 一种可光切换的大环离子对受体
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-06-16 Epub Date: 2026-04-23 DOI: 10.1039/d6qo00250a
Kuirong Fu , Hui Liu , Xinyan Mai , Zhiyao Yang , Muyun Tao , Song Qin , Yimin Cai , Xiaowei Li , Wen Feng , Lihua Yuan
{"title":"A photoswitchable macrocyclic ion-pair receptor","authors":"Kuirong Fu ,&nbsp;Hui Liu ,&nbsp;Xinyan Mai ,&nbsp;Zhiyao Yang ,&nbsp;Muyun Tao ,&nbsp;Song Qin ,&nbsp;Yimin Cai ,&nbsp;Xiaowei Li ,&nbsp;Wen Feng ,&nbsp;Lihua Yuan","doi":"10.1039/d6qo00250a","DOIUrl":"10.1039/d6qo00250a","url":null,"abstract":"<div><div>Achieving photoresponsive heteroditopic receptors capable of simultaneously binding and releasing ion-pairs under light irradiation remains a significant challenge, due to the difficulty in incorporating two distinct types of binding sites within a single cavity. Herein, we report the design and synthesis of a convergent heteroditopic azo-macrocycle that functions as a photoswitchable ion-pair receptor. This macrocycle incorporates an integrated cavity with amide-based cation- and anion-binding sites, bridged by photoisomerizable azobenzene units. Structural characterization, NMR titration studies, and DFT calculations reveal that the <em>trans</em>-isomer exhibits strong, cooperative binding for LiCl, with significant enhancement in affinity compared to individual ions. Upon UV-induced isomerization to the <em>Z</em>-form, binding is substantially weakened, enabling reversible capture and release of the ion-pair. Crucially, the receptor demonstrates highly selective solid–liquid extraction of LiCl from mixtures of alkali metal chlorides in a light-controlled manner. This work provides a strategic design for photoregulated ion-pair receptors and advances the development of smart extraction systems for lithium resource recovery.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 12","pages":"Pages 3628-3636"},"PeriodicalIF":0.0,"publicationDate":"2026-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147736068","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A metal- and solvent-free bromination of electron-deficient allyl and benzyl C–H bonds 缺电子烯丙基和苄基C-H键的无金属和无溶剂溴化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-06-16 Epub Date: 2026-04-23 DOI: 10.1039/d6qo00245e
Quanjin Rong , Qianhe Wang , Fan Wang , Zhong-Quan Liu , Xiaojing Liu
{"title":"A metal- and solvent-free bromination of electron-deficient allyl and benzyl C–H bonds","authors":"Quanjin Rong ,&nbsp;Qianhe Wang ,&nbsp;Fan Wang ,&nbsp;Zhong-Quan Liu ,&nbsp;Xiaojing Liu","doi":"10.1039/d6qo00245e","DOIUrl":"10.1039/d6qo00245e","url":null,"abstract":"<div><div>Bromination reactions of C(sp<sup>3</sup>)–H bonds at allylic and benzylic positions have been widely applied in the synthesis of pharmaceuticals and functional materials. However, traditional Wohl–Ziegler bromination reactions often involve harsh reaction conditions and afford low to moderate yields. In particular, direct bromination of electron-deficient allylic and benzylic C–H bonds has been rarely reported. Herein, we present an NHPI-catalyzed bromination method for electron-deficient allylic and benzylic C–H bonds. This method is metal- and solvent-free, exhibits high site selectivity and good yields, operates under mild conditions, and is operationally simple.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 12","pages":"Pages 3596-3601"},"PeriodicalIF":0.0,"publicationDate":"2026-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147736073","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A 4-nitro-3-arylpyrrole platform for the divergent synthesis of marine natural products: Ningalins and Lamellarins 4-硝基-3-芳基吡咯合成海洋天然产物：宁格林和片藻林的平台
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-06-16 Epub Date: 2026-04-20 DOI: 10.1039/d6qo00105j
Yihuan Yang , Guishun Bai , Jiajia Han , Mengyuan Wu , Yi Hua , Jianwei Chen , Jean Rodriguez , Damien Bonne , Hong Wang , Xiaoze Bao
{"title":"A 4-nitro-3-arylpyrrole platform for the divergent synthesis of marine natural products: Ningalins and Lamellarins","authors":"Yihuan Yang ,&nbsp;Guishun Bai ,&nbsp;Jiajia Han ,&nbsp;Mengyuan Wu ,&nbsp;Yi Hua ,&nbsp;Jianwei Chen ,&nbsp;Jean Rodriguez ,&nbsp;Damien Bonne ,&nbsp;Hong Wang ,&nbsp;Xiaoze Bao","doi":"10.1039/d6qo00105j","DOIUrl":"10.1039/d6qo00105j","url":null,"abstract":"<div><div>Pyrrole is a key structural motif found in numerous bioactive molecules and natural products. Herein, we report an efficient and scalable synthesis of polysubstituted 3-arylpyrroles <em>via</em> a Barton–Zard reaction between chloronitroalkenes and isocyanoacetates. The reaction was promoted by tetramethylguanidine in ethanol, tolerating a wide range of aryl and heteroaryl substituents, as well as sterically demanding groups. Mechanistic studies revealed a unique <em>in situ</em> transesterification pathway for specific isocyanoacetate derivatives. The synthetic utility of this methodology is further demonstrated through a concise, gram-scale total synthesis of marine natural products Ningalin B and Lamellarin L, underscoring its potential to accelerate the development of structurally related bioactive compounds.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 12","pages":"Pages 3589-3595"},"PeriodicalIF":0.0,"publicationDate":"2026-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147719962","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereospecific SuFEx reactivity of highly enantioenriched sulfondiimidoyl fluorides 高度富集对映体的磺胺二酰氟化物的立体定向SuFEx反应性
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-06-16 Epub Date: 2026-05-06 DOI: 10.1039/d6qo00230g
Glebs Jersovs , Aldis J. Pivars , Julija Bariseva , Vadims Kovada , Pavel A. Donets , Edgars Suna
{"title":"Stereospecific SuFEx reactivity of highly enantioenriched sulfondiimidoyl fluorides","authors":"Glebs Jersovs ,&nbsp;Aldis J. Pivars ,&nbsp;Julija Bariseva ,&nbsp;Vadims Kovada ,&nbsp;Pavel A. Donets ,&nbsp;Edgars Suna","doi":"10.1039/d6qo00230g","DOIUrl":"10.1039/d6qo00230g","url":null,"abstract":"<div><div>Sulfondiimidoyl fluorides are established SuFEx platforms, yet their potential in asymmetric synthesis remains largely unexplored. Herein we report stereospecific SuFEx transformations of highly enantioenriched sulfondiimidoyl fluorides to access sulfone diimines, sulfondiimidamides and sulfondiimidates with complete chirality transfer. For sulfone diimine formation, heteroleptic triorganozincates serve as mild and chemoselective carbon nucleophiles, enabling exclusive stereospecific allyl and benzyl transfer with broad functional group tolerance. The accomplished orthogonal deprotection of sulfondiimidoyl scaffolds demonstrates their additional synthetic flexibility. Collectively, this work establishes sulfondiimidoyl fluorides as robust chiral SuFEx building blocks for asymmetric synthesis.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 12","pages":"Pages 3735-3743"},"PeriodicalIF":0.0,"publicationDate":"2026-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148261587","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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