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How to Get Them on: N-Heterocyclic Carbenes (NHCs) on Surfaces 如何使它们在表面上：n -杂环碳烯（NHCs）上
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-02-09 DOI: 10.1002/hlca.202500201
Ankita Das, Preeti Chahar, Frank Glorius
{"title":"How to Get Them on: N-Heterocyclic Carbenes (NHCs) on Surfaces","authors":"Ankita Das,&nbsp;Preeti Chahar,&nbsp;Frank Glorius","doi":"10.1002/hlca.202500201","DOIUrl":"https://doi.org/10.1002/hlca.202500201","url":null,"abstract":"<div>\u0000 \u0000 <p>N-Heterocyclic carbenes (NHCs) have emerged as powerful and versatile surface-modifiers, forming robust and tunable metal–organic interfaces. Their controlled generation and attachment remain central to advancing NHC-based surface chemistry, as free carbenes are reactive species. This mini-review highlights current strategies for generating NHCs under conditions compatible with surface functionalization, including direct deprotonation of azolium salts, thermal activation of stable CO<sub>2</sub> and bicarbonate adducts, and emerging electrochemical methods. Here, the structure–reactivity relationships governing precursor stability and activation behavior, and their implementation in vacuum and solution environments, are discussed. Techniques used to study the modified surfaces are also briefly presented. Together, these developments provide a foundation for designing clean, well-defined NHC monolayers, enabling new opportunities in various domains, including catalysis, sensing, and molecular electronics.</p>\u0000 </div>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618168","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
Electron Donor–Acceptor Complexes Without Preinstalled Sacrificial Leaving Groups: Applications in Synthesis 没有预先安装的牺牲离去基的电子供体-受体配合物：在合成中的应用
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-13 DOI: 10.1002/hlca.202500168
Wenheng Liu, Line Næsborg
{"title":"Electron Donor–Acceptor Complexes Without Preinstalled Sacrificial Leaving Groups: Applications in Synthesis","authors":"Wenheng Liu,&nbsp;Line Næsborg","doi":"10.1002/hlca.202500168","DOIUrl":"https://doi.org/10.1002/hlca.202500168","url":null,"abstract":"<p>Electron donor–acceptor complexes provide a useful platform for photocatalyst-free radical generation under visible light irradiation and has emerged as a sustainable strategy for synthetic applications. Previous synthetic strategies based on EDA-complex formations are typically based on engineering leaving groups into the substrates to suppress back electron transfer that impedes forward reaction. However, such pre-functionalization affects efficiency and atom economy. This review highlights recent developments in the use of strategies for EDA-complex formations to induce photochemical coupling- and cyclization reactions that do not rely on preinstalled sacrificial leaving-groups. Most examples rely on alternative strategies to circumvent back electron transfer such as bond cleavage, oxygen-mediated oxidation, or excitation of EDA complex precursors. These studies illustrate the rising promise of EDA complexes without incorporation of sacrificial leaving-groups and highlight their potential as a broadly applicable, atom-economical platform for photocatalyst-free radical transformations in modern organic synthesis.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500168","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618113","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Sulfur Ylides in Skeletal-Editing—Ring Expansion Reactions 骨架编辑环扩张反应中的硫酰化物
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-02-04 DOI: 10.1002/hlca.202500194
Arsala Kamal, Olaf Tjabben, Ana Matošević, Olga García Mancheño
{"title":"Sulfur Ylides in Skeletal-Editing—Ring Expansion Reactions","authors":"Arsala Kamal,&nbsp;Olaf Tjabben,&nbsp;Ana Matošević,&nbsp;Olga García Mancheño","doi":"10.1002/hlca.202500194","DOIUrl":"https://doi.org/10.1002/hlca.202500194","url":null,"abstract":"<p>Sulfur ylides (S-ylides) have long been recognized as versatile reagents and intermediates in organic synthesis. In particular, their role as surrogates for diazo compounds has recently gained considerable attention due to their superior stability, safer handling, and broader functional group tolerance, which make them attractive alternatives in both academic and industrial settings. Beyond classical transformations, S-ylides have been increasingly applied in skeletal-editing strategies, such as ring expansion reactions, that provide access to pharmaceutically relevant frameworks. Despite these advances, challenges remain in developing highly enantioselective catalytic protocols and expanding the scope of sustainable photochemical methodologies. This perspective highlights the emerging potential of S-ylides in skeletal editing, tracing their evolution from fundamental studies to state-of-the-art applications, while offering insights into current limitations and future opportunities that could reshape their role in synthetic chemistry.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500194","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618025","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Colorimetric and Fluorimetric Multiple Metal Ion Sensing Using Naphthalene-Based Schiff Base 萘基席夫碱比色法和荧光法多金属离子传感
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-08 DOI: 10.1002/hlca.202500175
Jocelyn Pradegan, Aurélien Crochet, Katharina M. Fromm
{"title":"Colorimetric and Fluorimetric Multiple Metal Ion Sensing Using Naphthalene-Based Schiff Base","authors":"Jocelyn Pradegan,&nbsp;Aurélien Crochet,&nbsp;Katharina M. Fromm","doi":"10.1002/hlca.202500175","DOIUrl":"https://doi.org/10.1002/hlca.202500175","url":null,"abstract":"<p>A novel Schiff base ligand functionalized with a naphthalene moiety has been developed as colorimetric and fluorimetric sensor for the selective detection of multiple metal ions. The coordination of four metal ions (Fe<sup>2+</sup>, Fe<sup>3+</sup>, Co<sup>2+</sup>, and Ni<sup>2+</sup>) induces an individual color change in solution, while fluorescence is emitted upon the addition of seven other metal ions (Mg<sup>2+</sup>, Ca<sup>2+</sup>, Cd<sup>2+</sup>, Zn<sup>2+</sup>, Al<sup>3+</sup>, Ga<sup>3+</sup>, and In<sup>3+</sup>). The reliability of the chemosensor was evaluated through competition experiments with a panoply of different cations. The nature of the solvent was revealed to have an impact on the fluorescence properties but not on color changes, whereas the type of counterion did not influence the colorimetric and fluorimetric detection.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500175","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618079","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Developments on Diverse (Hetero)Arene Functionalization via Nucleophile-triggered Umpolung of (Hetero)Aryl Phosphonium Salts 通过亲核试剂触发的（杂）芳基磷盐的多（杂）芳烃功能化研究进展
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-18 DOI: 10.1002/hlca.202500223
Abhishek Dewanji, Priyasha Dey
{"title":"Recent Developments on Diverse (Hetero)Arene Functionalization via Nucleophile-triggered Umpolung of (Hetero)Aryl Phosphonium Salts","authors":"Abhishek Dewanji,&nbsp;Priyasha Dey","doi":"10.1002/hlca.202500223","DOIUrl":"https://doi.org/10.1002/hlca.202500223","url":null,"abstract":"<div>\u0000 \u0000 <p>Aryl and heteroaryl phosphonium salts have recently grabbed the attention of synthetic organic chemists as excellent substrates to obtain functionalized (hetero)arenes. The phosphonium moiety renders the adjoining carbon site electrophilic; therefore, they are good candidates for nucleophilic substitutions. The weakness of the C─P<sup>+</sup> bond paves the way for their activation via single electron reduction and thereby furnishing (hetero)aryl radicals for further functionalization. However, a rather intriguing but underexplored mode of activating the phosphonium salts has been via nucleophilic attack on the P<sup>+</sup>-center, resulting in the formation of the penta-coordinated phosphorane intermediates. These transient intermediates readily undergo fragmentation and give rise to (hetero)aryl anions suitable to be functionalized by reacting with appropriate electrophiles. Here we document the history and the recent advances of this umpolung strategy to project its potential for future applications.</p>\u0000 </div>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618107","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
Photocaged and Water-Soluble Glucose Functionalization for Spatiotemporal Acidification Pathways 时空酸化途径的光笼化和水溶性葡萄糖功能化
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-18 DOI: 10.1002/hlca.202500211
Nikolai Hempel, Michelle Szostak, Pol Besenius
{"title":"Photocaged and Water-Soluble Glucose Functionalization for Spatiotemporal Acidification Pathways","authors":"Nikolai Hempel,&nbsp;Michelle Szostak,&nbsp;Pol Besenius","doi":"10.1002/hlca.202500211","DOIUrl":"https://doi.org/10.1002/hlca.202500211","url":null,"abstract":"<p>The spatiotemporal control of complex molecular systems, such as chemical reaction networks (CRNs), requires reagents and reactive species that can be activated both efficiently and precisely. The design of CRNs has gained momentum as a strategy to investigate synthetic non-equilibrium systems that mimic key features of biological processes operating far from thermodynamic equilibrium. In this study, we present a novel photocleavable and water-soluble glucose–coumarin glycoside that bridges photochemical activation with chemical fuel-driven reactivity. During the optimization of the peracetylated glucose–coumarin glycoside synthesis, we elucidate the reaction mechanism of the Koenigs–Knorr glycosylation and identify the most likely rate-limiting step as the reversible formation of the orthoester. The photochemical release of glucose was subsequently used to drive an established model CRN based on glucose oxidase, enabling light-triggered acidification of the aqueous environment. Given the high water solubility of the coumarin-protected glucose derivative, our approach provides a versatile and easily implemented method for regulating pH-responsive processes and assemblies through precise optical control, in a range of aqueous buffered media.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500211","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Implementation of Large-Scale Multi-Reactor Automation for Process Development 工艺开发中大规模多反应器自动化的实现
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-10 DOI: 10.1002/hlca.202500120
Andreas Kaegi, Markus Spaeti, Jarred Blank
{"title":"Implementation of Large-Scale Multi-Reactor Automation for Process Development","authors":"Andreas Kaegi,&nbsp;Markus Spaeti,&nbsp;Jarred Blank","doi":"10.1002/hlca.202500120","DOIUrl":"https://doi.org/10.1002/hlca.202500120","url":null,"abstract":"<div>\u0000 \u0000 <p>Pharmaceuticals increasing complexity requires longer synthesis with unique processes for each step, increasing the number of experiments to develop robust sustainable processes. The time to develop these processes is getting shorter, and automation can support the growing need to efficiently perform more experiments. Automation reaction screening focuses more on small-scale high-throughput experimentation (HTE), which may not be applicable for late phase process development. To support these activities and decrease development time, we describe the implementation of a flexible large-scale multi-reactor automation platform for process development.</p>\u0000 </div>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618070","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
Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde With Alkyl Allyl Carbonates and Pd(II) Allyl-Amidinate 羰基烯丙基碳酸盐和烯丙基氨基酸Pd（II）选择性催化氧化苯甲醇制苯甲醛
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-03-15 Epub Date: 2026-01-08 DOI: 10.1002/hlca.202500160
Christian Ehinger, Mattia Ciuoli, Barnabé Berger, Christophe Copéret
{"title":"Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde With Alkyl Allyl Carbonates and Pd(II) Allyl-Amidinate","authors":"Christian Ehinger,&nbsp;Mattia Ciuoli,&nbsp;Barnabé Berger,&nbsp;Christophe Copéret","doi":"10.1002/hlca.202500160","DOIUrl":"https://doi.org/10.1002/hlca.202500160","url":null,"abstract":"<p>Group 9 and 10 amidinate complexes have been used as molecular precursors for surface organometallic chemistry (SOMC) and atomic layer deposition (ALD) because they readily react with OH functionalities, reversibly forming a metal oxygen bond. Here, we show that this reversible protonation step can be exploited to design a catalytic oxidation process of benzyl alcohol, where catalytic turnover is enabled by the addition of alkyl allyl carbonates in the presence of a catalytic amount of Pd(allyl)(DIA). Although overoxidation products are observed, we also present strategies to suppress their formation to obtain benzaldehyde in up to 95% yield. The presented work comprises a new strategy for the selective catalytic oxidation of alcohols to aldehydes, a fundamental reaction of organic chemistry.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500160","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147618078","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Detection of Radical Anions by Electrospray-Ionization Mass Spectrometry 电喷雾电离质谱法检测自由基阴离子
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-01-30 DOI: 10.1002/hlca.202500178
Niklas F. Eisele, Daniel Kösters, Konrad Koszinowski
{"title":"Detection of Radical Anions by Electrospray-Ionization Mass Spectrometry","authors":"Niklas F. Eisele,&nbsp;Daniel Kösters,&nbsp;Konrad Koszinowski","doi":"10.1002/hlca.202500178","DOIUrl":"https://doi.org/10.1002/hlca.202500178","url":null,"abstract":"<p>Radical anions constitute an important class of reactive intermediates. Here, we investigate the suitability of electrospray-ionization (ESI) mass spectrometry for their qualitative and quantitative analysis. To this end, we have probed solutions of 14 different benzoquinones and nitrobenzenes in the presence or absence of the reductant CoCp<sub>2</sub>. The latter greatly helped in the formation and detection of radical anions, but even without, analytes of sufficiently high electron affinity could accept an electron upon cathodic reduction during the ESI process and, thus, became observable. Analytes with low electron affinities escaped from detection because the corresponding radical anions did not form to a sufficient extent and/or underwent electron detachment during the ESI process and the consecutive ion transfer. Furthermore, we studied the effect of the analyte concentration, different reducing agents as well as the solvent and demonstrated the utility of the present approach for the mechanistic elucidation of reactions involving radical anions.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 2","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500178","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146217519","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Transannular O-Heterocyclization Reactions of Cyclododeca-1,5,9-triene Derivatives: A New Concept for the Preparation of Key Intermediates for Total Syntheses of Annonaceous Acetogenins 环十二烷-1,5,9-三烯衍生物的跨环o杂环化反应：制备全合成苯甲酸乙原关键中间体的新概念
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2026-01-14 DOI: 10.1002/hlca.202500185
Holger Schimanski, André Streiter, Micheline May, Oliver Mimkes, Johannes van Kempen, Constantin Daniliuc, Günter Haufe
{"title":"Transannular O-Heterocyclization Reactions of Cyclododeca-1,5,9-triene Derivatives: A New Concept for the Preparation of Key Intermediates for Total Syntheses of Annonaceous Acetogenins","authors":"Holger Schimanski,&nbsp;André Streiter,&nbsp;Micheline May,&nbsp;Oliver Mimkes,&nbsp;Johannes van Kempen,&nbsp;Constantin Daniliuc,&nbsp;Günter Haufe","doi":"10.1002/hlca.202500185","DOIUrl":"https://doi.org/10.1002/hlca.202500185","url":null,"abstract":"<p>Transannular π-cyclizations and heterocyclizations are characteristic for electrophilic addition reactions to medium-sized cycloalka-1,5-dienes. Transannular <i>O</i>-heterocyclizations have been frequently observed in reactions of cycloocta-1,5-diene and derivatives, but rarely for larger rings. Now this reaction type has been extended for diastereoisomeric cyclododeca-1,5,9-trienes to form 2,9-disubstituted 13-oxabicyclo[8.2.1]tridec-5-enes, creating four stereogenic centers in racemic form in one step. Ozonolytic cleavage of the remained double bond provided <i>cis</i>-1,5-dialkylated tetrahydrofuran derivatives bearing functional groups like halogen or hydroxyl in β- and β′-positions regarding the tetrahydrofuran-oxygen and carboxyl functions at the ends of both alkyl groups. Applying differently substituted cyclododeca-1,5-diene derivatives such as epoxides or vicinal diols as starting materials, diastereoisomers of the above-mentioned tetrahydrofurans have been prepared in four or five steps. These compounds have the potential to serve as Lego-like building blocks for syntheses of annonaceous acetogenins.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"109 2","pages":""},"PeriodicalIF":1.8,"publicationDate":"2026-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500185","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146217200","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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