Tetrahedron chemPub Date : 2024-08-14DOI: 10.1016/j.tchem.2024.100090
Jia-Cheng Li , Tian-Qi Hu , Zhou Xu , Bo Zhou , Long-Wu Ye
{"title":"Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones","authors":"Jia-Cheng Li , Tian-Qi Hu , Zhou Xu , Bo Zhou , Long-Wu Ye","doi":"10.1016/j.tchem.2024.100090","DOIUrl":"10.1016/j.tchem.2024.100090","url":null,"abstract":"<div><p>The one-carbon ring expansion of benzocyclobutenones is an efficient methodology for the assembly of cyclic ketones. However, hazardous reagents or noble metal catalysts are frequently required. Herein, we disclose a copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones, allowing the practical and atom-economical construction of diverse pyrryl 1-indanones in generally good yields under mild reaction conditions. This reaction represents an important advancement in the ring expansion of benzocyclobutenones <em>via</em> vinyl cation pathway.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100090"},"PeriodicalIF":0.0,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000299/pdfft?md5=23f3b40c0b3b57810a312b754ccef9c1&pid=1-s2.0-S2666951X24000299-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141997210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-08-01DOI: 10.1016/j.tchem.2024.100087
Rajiv Karmakar , Chhanda Mukhopadhyay
{"title":"l-Proline catalyzed synthesis of biologically promising heterocycles under sustainable conditions","authors":"Rajiv Karmakar , Chhanda Mukhopadhyay","doi":"10.1016/j.tchem.2024.100087","DOIUrl":"10.1016/j.tchem.2024.100087","url":null,"abstract":"<div><p>Catalysis field wherein a tiny organic molecule like <span><em>l</em></span>-proline is an efficient and selectively catalyzed organic reaction. Catalyst-supported organic synthesis is confirmed to be involved in the fast synthesis of novel compounds with selectivity and enhanced biological activities. <span><em>l</em></span>-proline catalyzed reactions are valuable tools for the making of different heterocycles, acyclic, and carbocyclic scaffolds that signify the main framework of most of the bio-active compounds. A few decades ago, novel tools for the manufacturing of bio-active molecules had a huge impact on organic chemistry. Subsequently, the synthesis of biologically important heterocycles through a synthetically proficient and environmentally benign route is the important purpose of modern synthetic chemistry. In this review, we discuss only <span><em>l</em></span>-proline catalyzed organic reactions (including condensation, addition, asymmetric, multi-components, and other modular reactions) for the sustainable synthesis of biologically promising heterocycles in a single trencher that may provide as a piece of reliable literature for further research in this field.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100087"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000263/pdfft?md5=7360970aaabda90d1ad3e7b8516a7217&pid=1-s2.0-S2666951X24000263-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141943434","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-08-01DOI: 10.1016/j.tchem.2024.100088
Mohammad Nuruzzaman , Zeinab M. Nizam , Jun Ohata
{"title":"Fluoroalcohols for chemical modification of biomolecules","authors":"Mohammad Nuruzzaman , Zeinab M. Nizam , Jun Ohata","doi":"10.1016/j.tchem.2024.100088","DOIUrl":"10.1016/j.tchem.2024.100088","url":null,"abstract":"<div><p>While their broad utility in various chemistry fields were well recognized for decades, fluoroalcohols have recently emerged as a unique solvent system for bioconjugation development. This review describes examples and roles of fluoroalcohols such as trifluoroethanol (TFE) and hexafluoroisopropanol (HFIP) for chemical modification of biomolecules such as polypeptides, nucleic acids, and saccharides. Many chemical modification processes were facilitated by notable functions of those fluoroalcohols such as a proton shuttle, reversible adduct formation with reactive species, and compatibility with electrochemistry/photochemistry. The usefulness of the fluoroalcohol solvents can be even promoted by its combination with a different solvent system for reaction enhancement and protein stabilization. The collection of the various chemical transformations in this review is an indication of the rapid growth of the solvent-assisted bioconjugation field.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100088"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000275/pdfft?md5=d9767242f2ace4ca37be9903a81b356c&pid=1-s2.0-S2666951X24000275-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141984624","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-08-01DOI: 10.1016/j.tchem.2024.100086
Peter Conen , Michael A.R. Meier
{"title":"Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions","authors":"Peter Conen , Michael A.R. Meier","doi":"10.1016/j.tchem.2024.100086","DOIUrl":"10.1016/j.tchem.2024.100086","url":null,"abstract":"<div><p>As a readily available and benign waste product of the petrochemical industry, elemental sulfur displays desirable characteristics as a raw material for new processes. Accordingly, the use of elemental sulfur as a reactant or reagent in synthetic organic chemistry receives continuous interest. The implementation of sulfur in synthetic procedures often necessitates the presence of basic or nucleophilic compounds, which are known to serve as activators, enabling a diverse range of transformations. However, the underlying mechanisms are still poorly understood, even for synthetically useful and well-established reactions that have been known for decades. While numerous reviews focus on the various types of products accessible via organic reactions involving elemental sulfur, this manuscript will put its emphasis on common mechanistic steps of these transformations, highlighting and discussing mechanistic studies and postulated pathways.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100086"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000251/pdfft?md5=5b2ca06c2ef7d0bd724e8a4b858a1e7c&pid=1-s2.0-S2666951X24000251-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141849795","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-07-17DOI: 10.1016/j.tchem.2024.100085
Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev
{"title":"Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study","authors":"Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev","doi":"10.1016/j.tchem.2024.100085","DOIUrl":"10.1016/j.tchem.2024.100085","url":null,"abstract":"<div><p>Herein we describe the novel approach to the synthesis of functionalized ind(az)olo-fused 1,2,4-thiadiazocine 1,1-dioxides through the CSIC (<em>Carbanion-mediated Sulfonate (Sulfonamide) Intermolecular Coupling (Intramolecular Cyclization</em>) reaction strategy. 1,2,4-Thiadiazocine 1,1-dioxides (put simply 8-membered <em>aza</em>sultams) are increasingly popular but quite underrepresented in the literature compounds, were prepared in two simple steps and good yield from readily available reagents. Particularly, the alkylation of 7-functionalized ind(az)oles with <em>N</em>-(chloromethyl)-<em>N</em>-methylmethanesulfonamide gave the corresponding <em>N</em>-((1<em>H</em>-ind(az)ol-1-yl)methyl)-<em>N</em>-methylmethane-sulfonamides which underwent base-mediated cyclization affording the target 8-membered <em>aza</em>sultams. The method worked well and provided <em>aza</em>sultams decorated with a set of synthetically valuable handles. The conducted DFT calculations explained and rationalized the experimental data thus allowing us to formulate the rules of the structure‒activity relationship. Despite the prepared compounds showing weak cytotoxicity against the MDA-MB-231 breast cancer cell line, they are considered novel building blocks and perspective pharmacological templates prone to further optimization.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100085"},"PeriodicalIF":0.0,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X2400024X/pdfft?md5=8a5acacf07f97bf098fa955907034fa1&pid=1-s2.0-S2666951X2400024X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141728620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-07-10DOI: 10.1016/j.tchem.2024.100084
Hiroshige Ogawa, Hugh Nakamura
{"title":"Atroposelective total synthesis of strecintide 839","authors":"Hiroshige Ogawa, Hugh Nakamura","doi":"10.1016/j.tchem.2024.100084","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100084","url":null,"abstract":"<div><p>The first total synthesis of the recently isolated strecintide 839 is reported. Strecintide 839 is one of the RiPP natural products that have been vigorously isolated in recent years and is known to possess the extremely rare and highly strained atrop-Trp-Trp linkage. This study details the comprehensive investigation into the construction of the highly strained atrop-Trp-Trp linkage and its application in the total synthesis of strecintide 839.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100084"},"PeriodicalIF":0.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000238/pdfft?md5=030aa36d47ed9088ca853406782b001e&pid=1-s2.0-S2666951X24000238-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141607762","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-07-05DOI: 10.1016/j.tchem.2024.100081
Ronit S. Bernard , Ajit Kumar Jha , Marcin Kalek
{"title":"Electrochemical oxidations through hypervalent iodine redox catalysis","authors":"Ronit S. Bernard , Ajit Kumar Jha , Marcin Kalek","doi":"10.1016/j.tchem.2024.100081","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100081","url":null,"abstract":"<div><p>In recent years, a growing number of oxidations that involve electrochemical regeneration of catalytic hypervalent iodine species has been developed. These transformations benefit from the combination of rich reactivity offered by hypervalent iodine compounds and sustainability advantage provided by electrocatalysis, which eliminates the need for any stoichiometric redox reagents. This review provides a systematic overview of this emerging field, covering the most abundant two-electron electrocatalysis with iodoarenes via I(I)/I(III) redox cycle, the isolated existing example of I(V)/I(VII) cycle, and a newly developed approach exploiting iodoarenes as I(I)/I(II) single-electron transfer mediators.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100081"},"PeriodicalIF":0.0,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000202/pdfft?md5=9e1b9a3fd8e3b72f0ea145bc80235b83&pid=1-s2.0-S2666951X24000202-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141594270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-07-04DOI: 10.1016/j.tchem.2024.100083
Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu
{"title":"Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction","authors":"Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu","doi":"10.1016/j.tchem.2024.100083","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100083","url":null,"abstract":"<div><p>Asymmetric carbohydroxylation of alkenes offers an efficient approach to access chiral alcohols, a class of versatile building blocks in pharmaceutical and agrochemical industries, from abundant simple alkenes. Herein we reported a sequential photo-biocatalysis protocol for the asymmetric carbohydroxylation of alkenes, involving a stepwise photocatalytic decarboxylative radical addition/Kornblum oxidation and enzymatic reduction. A series of chiral alcohols with bulky structures were synthesized in up to 75 % isolated yields and 99 % ee from <em>N-</em>hydroxyphthalimide esters and aryl alkenes.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100083"},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000226/pdfft?md5=0a3f1b332418a2bdbabd201092a6755e&pid=1-s2.0-S2666951X24000226-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141582847","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-07-03DOI: 10.1016/j.tchem.2024.100082
Meng-Die Li, Xin-Ru Wang, Tao-Yan Lin
{"title":"Recent advances in copper-catalyzed asymmetric propargylic substitution","authors":"Meng-Die Li, Xin-Ru Wang, Tao-Yan Lin","doi":"10.1016/j.tchem.2024.100082","DOIUrl":"10.1016/j.tchem.2024.100082","url":null,"abstract":"<div><p>Copper-catalyzed enantioselective propargylic substitution has become an increasingly reliable strategy to construct stereogenic centers over the past two decades. Currently, various catalytic systems and reaction modes have been developed for the synthesis of different chiral propargylic frameworks. Therein, stereochemical control can be achieved either through the nucleophilic addition at the γ-site of the copper-allenylidene intermediate, or the newly proposed nucleophilic addition of copper-vinylvinylidene intermediate comprising two reactive sites (γ, ε). This review briefly summarizes the development of copper-catalyzed asymmetric propargylic substitution on a variety of different substrates, including but not limited to propargylic esters, cyclic carbonates and carbamates, and yne-allylic esters.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100082"},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000214/pdfft?md5=1aa6ee4010e77652e0d8df77e22de44f&pid=1-s2.0-S2666951X24000214-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141636807","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tetrahedron chemPub Date : 2024-06-27DOI: 10.1016/j.tchem.2024.100080
Sheng Zhang, Man-Bo Li
{"title":"Repurposing HER catalysis toward metal hydride-mediated electro-reductive transformations","authors":"Sheng Zhang, Man-Bo Li","doi":"10.1016/j.tchem.2024.100080","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100080","url":null,"abstract":"<div><p>Hydrogen evolution reaction (HER) is known as one of the most cardinal reactions in energy chemistry. In the field, tremendous efforts have been devoted to discovering highly efficient catalysts and investigating the reaction mechanism. Metal hydrides are the most critical intermediates in the HER catalysis, and they also exhibit versatile reactivity in organic transformations. Redirecting HER catalysis for metal hydride-mediated electrochemical transformations would provide effective solutions for some challenging issues in conventional organic chemistry. Although some remarkable progress has recently been achieved in the cross-subject, the synthetic chemistry community has yet to fully understand the related catalytic mechanism and catalyst design. Herein, we conclude the catalytic HER mechanism and catalyst design principles to facilitate the repurposing HER catalysis toward organic electrochemistry. Recent examples of metal hydride-mediated electro-reductive transformations have also been covered, including the reduction of unsaturated bonds and the functionalization of C–H bonds. Additionally, we discussed challenges and future developments in the field.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100080"},"PeriodicalIF":0.0,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000196/pdfft?md5=69ceaa5807bacf0325ed1656a32e9535&pid=1-s2.0-S2666951X24000196-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141486682","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}