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Organic chemistry frontiers : an international journal of organic chemistry最新文献

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N-Pechmann aza-BODIPYs: enhanced near-infrared photothermal conversion by the cross-conjugated structure N-Pechmann aza-BODIPYs：通过交叉共轭结构增强近红外光热转换
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-17 DOI: 10.1039/d6qo00024j
Yuma Tanaka , Yuya Taninokuchi , Taichi Sawamura , Saori Okamura , Shigeki Mori , Masatoshi Ishida , Koji Miki , Kouichi Ohe , Takanori Iwasaki , Soji Shimizu
{"title":"N-Pechmann aza-BODIPYs: enhanced near-infrared photothermal conversion by the cross-conjugated structure","authors":"Yuma Tanaka ,&nbsp;Yuya Taninokuchi ,&nbsp;Taichi Sawamura ,&nbsp;Saori Okamura ,&nbsp;Shigeki Mori ,&nbsp;Masatoshi Ishida ,&nbsp;Koji Miki ,&nbsp;Kouichi Ohe ,&nbsp;Takanori Iwasaki ,&nbsp;Soji Shimizu","doi":"10.1039/d6qo00024j","DOIUrl":"10.1039/d6qo00024j","url":null,"abstract":"<div><div>Near-infrared (NIR) photothermal conversion was achieved with the dimeric aza-BODIPY analogue called NPAB-55, which features a cross-conjugated, exocyclic double bond to enhance thermal decay from the excited states. NPAB-55 was synthesized according to the Schiff base-forming synthetic protocol using a 5,5-membered N-Pechmann dye. Due to the thermal isomerization to a 6,6-membered N-Pechmann structure during the reaction, NPAB-66, exhibiting intense fluorescence in the visible region in contrast to the non-fluorescent NPAB-55, was also obtained. The photothermal conversion capabilities of NPAB-55 were investigated as nanoparticles fabricated with PEG-PLGA polymers. Due to their high photothermal conversion efficiency of 47% and photothermal stability, the NPAB-55 nanoparticles exhibited reasonable photoacoustic response and photothermal cytotoxicity against cancer cells upon NIR illumination.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2309-2315"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146223425","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
Divergent transformations of N-phenyl-N-tosylfluoroacetamides to amides and imides (N-tosylamides) n -苯基- n - tosylfluoracetamide向酰胺和亚胺（N-Tosylamides）的发散转化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-24 DOI: 10.1039/d6qo00069j
Nan Wang , Xia Chen , Chun-Yan Liu , Zhi-Ying Feng , Ming Bao , Xiao-Yu Zhou
{"title":"Divergent transformations of N-phenyl-N-tosylfluoroacetamides to amides and imides (N-tosylamides)","authors":"Nan Wang ,&nbsp;Xia Chen ,&nbsp;Chun-Yan Liu ,&nbsp;Zhi-Ying Feng ,&nbsp;Ming Bao ,&nbsp;Xiao-Yu Zhou","doi":"10.1039/d6qo00069j","DOIUrl":"10.1039/d6qo00069j","url":null,"abstract":"<div><div>The strained C–N bond of <em>N</em>-phenyl-<em>N</em>-tosylfluoroacetamides is activated <em>via</em> a transition-metal-free nucleophilic addition pathway by employing suitable nucleophilic reagents, such as indoles, indolines, aryl amines and carboxylic acids. Based on this, two efficient and convenient approaches are developed for the synthesis of amides by utilizing divergent fragments of <em>N</em>-phenyl-<em>N</em>-tosylfluoroacetamides in this study. The reaction of nitrogen-containing compounds and carboxylic acids with <em>N</em>-phenyl-<em>N</em>-tosylfluoroacetamides proceeded smoothly in the presence of a base to afford diverse fluoroacetamides and <em>N</em>-tosylamides in satisfactory-to-excellent yields. <em>N</em>-Phenyl-<em>N</em>-tosylfluoroacetamides served as integrated reagents to provide either a fluoroacetyl or amine source, depending on the substrate with which they were reacted. These protocols are amenable to scale up. Various groups, including the synthetically useful functional groups Br, NO<sub>2</sub>, OH and CO<sub>2</sub>Me, were tolerated well under the current reaction conditions.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2466-2472"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279542","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
EtAlCl2-promoted defluorinative thiolation of α-trifluoromethyl alkenes EtAlCl2促进α-三氟甲基烯烃的脱氟硫代化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-03-02 DOI: 10.1039/d6qo00011h
Xin Guo , Guoliang Pu , Long Xiao , Jiarui Liang , Hang Zhang , Yu Chen , Yang Huang , Qiuli Yao , Chun-Yang He
{"title":"EtAlCl2-promoted defluorinative thiolation of α-trifluoromethyl alkenes","authors":"Xin Guo ,&nbsp;Guoliang Pu ,&nbsp;Long Xiao ,&nbsp;Jiarui Liang ,&nbsp;Hang Zhang ,&nbsp;Yu Chen ,&nbsp;Yang Huang ,&nbsp;Qiuli Yao ,&nbsp;Chun-Yang He","doi":"10.1039/d6qo00011h","DOIUrl":"10.1039/d6qo00011h","url":null,"abstract":"<div><div>Here, we report a EtAlCl<sub>2</sub>-promoted thiolation of trifluoromethyl alkenes, which leads to the complete substitution of all three fluorine atoms and affords trisubstituted products. Although the transformation proceeds through a three-step sequence, it maintains high efficiency and delivers the target product in good to excellent yields. Mechanistic studies indicate that the reaction initially forms a <em>gem</em>-difluoroalkene intermediate. The newly introduced thioether group then activates the remaining C–F bonds, thereby facilitating subsequent substitution to afford the trisubstituted products.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2487-2492"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147330082","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
Cu(i)-catalyzed 1,2-carbofluorination of unactivated alkenes enabled by N-fluorobenzamides via free radical relay Cu(I)催化的n -氟苯酰胺通过自由基接力使未活化烯烃1,2-碳氟化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-03-02 DOI: 10.1039/d5qo01763g
Hong Ji , Haifeng Qiao , Boyi Wang , Tianyu Lu , Weixing Chang , Lingyan Liu , Jing Li
{"title":"Cu(i)-catalyzed 1,2-carbofluorination of unactivated alkenes enabled by N-fluorobenzamides via free radical relay","authors":"Hong Ji ,&nbsp;Haifeng Qiao ,&nbsp;Boyi Wang ,&nbsp;Tianyu Lu ,&nbsp;Weixing Chang ,&nbsp;Lingyan Liu ,&nbsp;Jing Li","doi":"10.1039/d5qo01763g","DOIUrl":"10.1039/d5qo01763g","url":null,"abstract":"<div><div>The construction of carbon–fluorine bonds has long been a challenging task. This work presents a two-component 1,2-carbofluorination bifunctionalization of unactivated alkenes <em>via</em> a radical-relay process. <em>N</em>-Fluorobenzamide was employed as a unique carbofluoro-bifunctional reagent that adds across unactivated alkenes, enabling simultaneous formation of C–C and C–F bonds. The reaction proceeds through homolytic cleavage of the N–F bond to generate a nitrogen-centered radical, followed by a 1,5-H atom transfer to produce a remote benzylic carbon radical. This carbon radical adds to the alkene, forming a new alkyl radical, which then undergoes single-electron transfer mediated by an active copper species, ultimately affording a series of β-fluoroamides in moderate yields. Notable features of this transformation include excellent atom economy (with no atom loss), mild reaction conditions and operational simplicity.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2473-2478"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147330084","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
α-Functionalization of ethers with acridanes and amines via metal-free direct C(sp3)–H radical–radical cross-dehydrogenative coupling 无金属直接C(sp3)-H自由基-自由基交叉脱氢偶联对吖啶烷和胺类醚α-功能化的影响
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-17 DOI: 10.1039/d6qo00065g
Sudip Karmakar , Sumit Das , Koushik Naskar , Imtiaj Mondal , Moumita Chowdhury , Ronaldo Nongmaithem , Indubhusan Deb
{"title":"α-Functionalization of ethers with acridanes and amines via metal-free direct C(sp3)–H radical–radical cross-dehydrogenative coupling","authors":"Sudip Karmakar ,&nbsp;Sumit Das ,&nbsp;Koushik Naskar ,&nbsp;Imtiaj Mondal ,&nbsp;Moumita Chowdhury ,&nbsp;Ronaldo Nongmaithem ,&nbsp;Indubhusan Deb","doi":"10.1039/d6qo00065g","DOIUrl":"10.1039/d6qo00065g","url":null,"abstract":"<div><div>Metal-free, direct radical–radical cross-dehydrogenative coupling (CDC) of the relatively unactivated C(sp<sup>3</sup>)–H bond of ethers with the C(sp<sup>3</sup>)–H bond of acridanes and amines has been developed, enabling the construction of C9-etherified acridanes and α-etherified amines in moderate to excellent yields using <em>tert</em>-butyl hydroperoxide (TBHP) as the sole oxidant. Mechanistic investigations, including characterization of the TEMPO-adduct by single crystal X-ray analysis and isotope-labeling experiments, further substantiate the radical–radical coupling pathway.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2437-2443"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146222998","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
Visible light-induced regioselective/dehydrogenative C–H silylation of (thio)chromones via a tricatalytic process 可见光诱导的三催化（Thio）铬的区域选择性/脱氢硅基化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-11 DOI: 10.1039/d6qo00081a
Shou-Cai Wang , Zi-Ren Chen , Fei Xue , Yong-Hong Zhang , Bin Wang , Shao-Feng Wu , Yu Xia , Weiwei Jin , Fanghua Ji , Chenjiang Liu
{"title":"Visible light-induced regioselective/dehydrogenative C–H silylation of (thio)chromones via a tricatalytic process","authors":"Shou-Cai Wang ,&nbsp;Zi-Ren Chen ,&nbsp;Fei Xue ,&nbsp;Yong-Hong Zhang ,&nbsp;Bin Wang ,&nbsp;Shao-Feng Wu ,&nbsp;Yu Xia ,&nbsp;Weiwei Jin ,&nbsp;Fanghua Ji ,&nbsp;Chenjiang Liu","doi":"10.1039/d6qo00081a","DOIUrl":"10.1039/d6qo00081a","url":null,"abstract":"<div><div>Direct C–H silylation of (thio)chromones was achieved by the combination of hydrogen atom transfer (HAT), photoredox and transition-metal catalysis under ambient air conditions. High regioselectivity, oxidant- and noble-metal-free conditions, and synergistic multiple catalysis were the major features of this protocol. Moreover, this approach can be safely conducted on the gram scale with hydrogen as the sole byproduct.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2388-2393"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146160911","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
Synergistic experimental and theoretical investigation of carbazole–cyanopyridine-based hole-transporting materials 咔唑-氰吡啶基空穴输运材料协同实验与理论研究
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-17 DOI: 10.1039/d6qo00076b
Rachel Chetri , Vygintas Jankauskas , Gediminas Kreiza , Kasparas Rakstys , Vytautas Getautis , Rahim Ghadari , Arijit Saha , Ahipa Tantri Nagaraja
{"title":"Synergistic experimental and theoretical investigation of carbazole–cyanopyridine-based hole-transporting materials","authors":"Rachel Chetri ,&nbsp;Vygintas Jankauskas ,&nbsp;Gediminas Kreiza ,&nbsp;Kasparas Rakstys ,&nbsp;Vytautas Getautis ,&nbsp;Rahim Ghadari ,&nbsp;Arijit Saha ,&nbsp;Ahipa Tantri Nagaraja","doi":"10.1039/d6qo00076b","DOIUrl":"10.1039/d6qo00076b","url":null,"abstract":"<div><div>This work highlights the design, synthesis, and characterization of three new hole-transporting materials (, , and ) based on donor–acceptor–donor (D–A–D) and acceptor–acceptor–donor (A–A–D) concepts. Crystals of two compounds, and , were obtained under similar crystallization conditions. The molecular structures were thoroughly examined using DFT, photophysical, electrochemical, and thermal methods. The UV-vis absorption spectrum of displayed a significant bathochromic effect compared to its counterparts and . This could be because the thiophene units enhance conjugation and lead to a bathochromic shift. Compared to (1.7 × 10<sup>−5</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>) and (1.6 × 10<sup>−5</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>), was found to have a higher hole mobility value of 2.1 × 10<sup>−5</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>. To further explain and complement the experimental data, DFT calculations of the geometry, electronic structure, absorption, reorganization energy, transition density matrix, and density of states of compounds were performed. These characteristics make it abundantly evident that compounds based on carbazoles and cyanopyridines are very attractive materials for use as hole-transporting materials in perovskite solar cells.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2367-2381"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146222993","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
Pd(ii)-catalyzed aerobic dual C–N bond formation: oxygen-dependent divergence between dihydroquinazolinone and aza-Michael pathways, an experimental and computational study Pd(II)-催化的有氧双C-N键形成：二氢喹唑啉酮和Aza-Michael途径之间的氧依赖差异，实验和计算研究
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-06 DOI: 10.1039/d5qo01381j
Narges Mohammadi , Farnaz Jafarpour , Leyla Mohammadkhani , Alireza Ariafard
{"title":"Pd(ii)-catalyzed aerobic dual C–N bond formation: oxygen-dependent divergence between dihydroquinazolinone and aza-Michael pathways, an experimental and computational study","authors":"Narges Mohammadi ,&nbsp;Farnaz Jafarpour ,&nbsp;Leyla Mohammadkhani ,&nbsp;Alireza Ariafard","doi":"10.1039/d5qo01381j","DOIUrl":"10.1039/d5qo01381j","url":null,"abstract":"<div><div>We report an aerobic three-component reaction of isatoic anhydrides, anilines, and acrylamides that simultaneously forms two distinct C–N bonds through two sequential Pd(<span>ii</span>)-catalyzed cycles, affording 2,3-dihydroquinazolin-4(1<em>H</em>)-ones (DHQs) incorporating β-amino carbonyl motifs. The presence of O<sub>2</sub> is essential for the chemoselective formation of DHQs; in its absence, the reaction instead affords the competing aza-Michael adduct. To understand the origin of this chemoselectivity, we investigated the mechanistic details of the reaction using DFT calculations. Our results reveal that, in the pathway leading to DHQs, the first C–N bond is formed through a Pd(<span>ii</span>)-catalyzed oxidative C–H/N–H coupling, for which O<sub>2</sub> is indispensable. O<sub>2</sub> reacts with a Pd–H intermediate formed in the cycle, generating a Pd–hydroperoxide species that promotes catalyst turnover <em>via</em> H<sub>2</sub>O<sub>2</sub> release. The second C–N bond is then formed through an intramolecular nucleophilic addition, furnishing the cyclic DHQ scaffold.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2331-2340"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146139049","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
Organocatalytic asymmetric synthesis of fluorinated pyranopyrazoles 氟化吡喃吡唑的有机催化不对称合成
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-14 DOI: 10.1039/d6qo00005c
Jianfeng Mu , Aining Dong , Menghan Yang , Hongyu Zhang , Guoshun Zhang , Xiaochen Wang , Bei Wei , Shurong Ban
{"title":"Organocatalytic asymmetric synthesis of fluorinated pyranopyrazoles","authors":"Jianfeng Mu ,&nbsp;Aining Dong ,&nbsp;Menghan Yang ,&nbsp;Hongyu Zhang ,&nbsp;Guoshun Zhang ,&nbsp;Xiaochen Wang ,&nbsp;Bei Wei ,&nbsp;Shurong Ban","doi":"10.1039/d6qo00005c","DOIUrl":"10.1039/d6qo00005c","url":null,"abstract":"<div><div>Asymmetric fluorinated pyranopyrazoles were successfully constructed with good yields (up to 85%) and high enantioselectivity (up to 93% ee) <em>via</em> the reaction of unsaturated pyrazolones with α-trifluoromethyl β-fluorinated <em>gem</em>-diols, a method that effectively avoids detrifluoroacetylation. Furthermore, the absolute configuration of the products was unambiguously confirmed by X-ray crystallographic analysis, providing reliable structural evidence for the asymmetric transformation.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2424-2429"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146184557","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
β- and Z-selective metal-free cyanation of ynamides: a direct approach to piperidines fused to arenes 氨基酰胺的β- z选择性无金属氰化反应：与芳烃融合的哌啶的直接方法
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-04-21 Epub Date: 2026-02-24 DOI: 10.1039/d6qo00022c
Dorian Schutz , Wenwen Yang , Laurence Miesch
{"title":"β- and Z-selective metal-free cyanation of ynamides: a direct approach to piperidines fused to arenes","authors":"Dorian Schutz ,&nbsp;Wenwen Yang ,&nbsp;Laurence Miesch","doi":"10.1039/d6qo00022c","DOIUrl":"10.1039/d6qo00022c","url":null,"abstract":"<div><div>Metal-free β- and <em>Z</em>-selective hydrocyanation of terminal ynamides using TMSCN and TBAF is described. The transformation proceeds with excellent regio- and stereoselectivity, delivering exclusively <em>Z</em>-configured tertiary enamides. Treatment with TMSOTf promotes clean <em>Z</em> to <em>E</em> isomerization. Simultaneous activation of the nitrile moiety by TMSOTf in the presence of an internal nucleophile induces intramolecular cyclization, yielding piperidine frameworks. The reaction accommodates a range of nucleophiles, enabling the synthesis of structurally diverse and previously inaccessible heterocyclic scaffolds.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 8","pages":"Pages 2459-2465"},"PeriodicalIF":0.0,"publicationDate":"2026-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279582","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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