Chinese Journal of Chemistry最新文献

{"title":"Repurposing Naturally Occurring Enzymes Using Visible Light","authors":"Yuanyuan Xu,&nbsp;Fulu Liu,&nbsp;Beibei Zhao,&nbsp;Xiaoqiang Huang","doi":"10.1002/cjoc.202400656","DOIUrl":"https://doi.org/10.1002/cjoc.202400656","url":null,"abstract":"<div>\u0000 \u0000 \u0000 <section>\u0000 \u0000 <p>Enzymes are natural treasure troves that hold multiple superiority. Enzymatic catalysis has become a powerful tool for asymmetric synthesis, though it is typically limited to a relatively narrow range of reaction types. By integrating the advantages of enzymatic catalysis with photocatalysis, photoenzymatic catalysis not only expands the catalytic capabilities of enzymes but also provides an effective strategy for the stereo-control of photochemical reactions, thereby emerging as a significant research field. Herein, we focus on new-to-nature photoenzymatic catalysis by repurposing naturally occurring enzymes with visible light. We highlight the seminal work in reshaping various classes of enzymes, emphasizing their catalytic mechanism and synthetic potentials.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Early Day Record</h3>\u0000 \u0000 <p></p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3553-3558"},"PeriodicalIF":5.5,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641154","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}

{"title":"Structurally Diverse Limonoids from Trichilia connaroides and Their Antitumor Activities","authors":"Ying Yan,&nbsp;Dan Wang,&nbsp;Fang-Jiao Zhou,&nbsp;Yu-Han Zhao,&nbsp;Xu-Jie Qin,&nbsp;Yu Zhang,&nbsp;Xiao Ding,&nbsp;Xiao-Jiang Hao","doi":"10.1002/cjoc.202400923","DOIUrl":"https://doi.org/10.1002/cjoc.202400923","url":null,"abstract":"<div>\u0000 \u0000 <p>Twelve new limonoids (<b>1</b>—<b>12</b>), named trichilitins A—L, were isolated from the leaves and twigs of <i>Trichilia connaroides</i>, together with ten known compounds (<b>13</b>—<b>22</b>). The structures were elucidated by extensive spectroscopic investigations, X-ray diffraction analyses, and ECD calculations. Compound <b>1</b>, which belongs to a unique class of ring B-<i>seco</i> limonoid, has been identified as 6/7/6/5 tetracyclic due to a key Baeyer-Villiger oxidation. Compounds <b>2</b>—<b>7</b> were identified as ring intact limonoids, while compounds <b>8</b>—<b>10</b> were established as ring D-<i>seco</i> ones, and <b>11</b> and <b>12</b> were determined to be rearranged ones. All of the compounds were tested for cytotoxicity against three human tumor cell lines (HCT-116, NCl-H1975, and SH-SY5Y). Compounds <b>6</b>, <b>7</b>, <b>13</b>, <b>14</b>, and <b>19</b> exhibited significant cytotoxic effects, especially <b>7</b> exhibited significant cytotoxic effects against HCT-116 with an IC₅₀ value of 0.035 μmol·L^–1 and was more active than the positive control, doxorubicin with an IC₅₀ value of 0.20 μmol·L^–1. Compound <b>7</b> effectively induced apoptosis of HCT-116, which was associated with S-phase cell cycle arrest. Furthermore, the Western blot analysis showed that compound <b>7</b> could induce cell cycle arrest by promoting the expression levels of p53 and p21.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3567-3580"},"PeriodicalIF":5.5,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641356","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}

{"title":"Inside Cover Picture","authors":"","doi":"10.1002/cjoc.202490232","DOIUrl":"https://doi.org/10.1002/cjoc.202490232","url":null,"abstract":"<p>Pyridine and piperidine are common structural motifs in natural products and pharmaceutical compounds, underscoring the importance of their synthesis. Our group has developed chiral spiro-bicyclic bisborane catalysts that enable the efficient and highly enantioselective reduction of pyridines to chiral piperidines. Subsequent transformations allow the conversion of the piperidine products into bioactive natural products. More details are discussed in the article by Wang <i>et al</i>. on pages 3088—3092.\u0000\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2942"},"PeriodicalIF":5.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cjoc.202490232","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142561540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cross-Electrophile Couplings (XECs) between Similar Electrophile Reagents","authors":"Jie Lei,&nbsp;Shan Yu,&nbsp;Zhi-Gang Xu","doi":"10.1002/cjoc.202400684","DOIUrl":"https://doi.org/10.1002/cjoc.202400684","url":null,"abstract":"<div>\u0000 \u0000 <section>\u0000 \u0000 <h3> Comprehensive Summary</h3>\u0000 \u0000 <p>Cross-electrophile couplings (XEC), a crucial subset of cross-coupling reactions, center on the formation of robust C—C bonds through the union of two electrophiles. Usually, such reactions have primarily been catalyzed by transition metals. However, with the steady advancements in photochemical and electrochemical technologies, XEC reactions have significantly progressed and broadened their scope, allowing for the utilization of a wider array of tolerable functional groups, thus revealing vast application prospects. This review aims to systematically summarize the current prevalent types of electrophiles and delve into their specific application examples within XEC reactions involving electrophiles with identical functional groups. Specifically, XECs between the same type of halides have received considerable attention, whereas carboxylic acids and alcohols are still in the early stages of investigation. Furthermore, certain other common electrophiles remain unexplored in this context. Moreover, this review underscores the remarkable contributions of photochemistry and electrochemistry in the field of XEC reactions, aiming to provide valuable insights and inspiration for researchers. Also, this review hopes to spark further interest in XEC reactions, thereby fueling the continuous development and advancement of this exciting area of research.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p>Since the 1960s, advancements in the XEC reaction have been substantial, driven primarily by the application of transition metal catalysts. In this area, many distinguished scientists have contributed their wisdom and efforts. Particularly noteworthy is that, during the systematic study of XEC reactions with the identical functional groups, in 2016, MacMillan achieved a photocatalytic XEC reaction between aryl bromides and alkyl bromides; in 2020, Weix successfully realized a nickel-catalyzed XEC reaction between aryl chlorides and alkyl chlorides. Concurrently, contributions from researchers such as Mei, Wolf, Sevov, Lin, Shen, Browne, Zhang, and Qiu have expanded the scope of XEC reactions to various halides. By 2022, MacMillan and Baran achieved a significant milestone in the XEC between carboxylic acids, further broadening the scope of research in this area. Also, advancements in the XEC of alcohols have been noted, with researchers including Weix, Lian, Tu, and Stahl conducting pioneering work and successfully executing the XEC of protective groups. It is foreseen that the ongoing research endeavors will primarily concentrate on the expansion of diverse electrophiles.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3518-3532"},"PeriodicalIF":5.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641232","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}

{"title":"Electrolyte Effects in Electrocatalytic Kinetics†","authors":"Xiao-Yu Li,&nbsp;Zhi-Ming Zhang,&nbsp;Xin-Xin Zhuang,&nbsp;Ze-Tong Jia,&nbsp;Tao Wang","doi":"10.1002/cjoc.202400458","DOIUrl":"https://doi.org/10.1002/cjoc.202400458","url":null,"abstract":"&lt;div&gt;\u0000 \u0000 &lt;section&gt;\u0000 \u0000 &lt;h3&gt; Comprehensive Summary&lt;/h3&gt;\u0000 \u0000 &lt;p&gt;Tuning electrolyte properties is a widely recognized strategy to enhance activity and selectivity in electrocatalysis, drawing increasing attention in this domain. Despite extensive experimental and theoretical studies, debates persist about how various electrolyte components influence electrocatalytic reactions. We offer a concise review focusing on current discussions, especially the contentious roles of cations. This article further examines how different factors affect the interfacial solvent structure, particularly the hydrogen-bonding network, and delves into the microscopic kinetics of electron and proton-coupled electron transfer. We also discuss the overarching influence of solvents from a kinetic modeling perspective, aiming to develop a robust correlation between electrolyte structure and reactivity. Lastly, we summarize ongoing research challenges and suggest potential directions for future studies on electrolyte effects in electrocatalysis.&lt;/p&gt;\u0000 \u0000 &lt;p&gt;\u0000 &lt;/p&gt;\u0000 &lt;/section&gt;\u0000 \u0000 &lt;section&gt;\u0000 \u0000 &lt;h3&gt; Key Scientists&lt;/h3&gt;\u0000 \u0000 &lt;p&gt;In 1956, Marcus theory was developed to describe the mechanism of outer-sphere electron transfer (OS-ET). In 1992, Nocera &lt;i&gt;et al.&lt;/i&gt; directly measured proton-coupled electron transfer (PCET) kinetics for the first time, and their subsequent research in 1995 investigated the effects of proton motion on electron transfer (ET) kinetics. In 1999 and 2000, Hammes-schiffer &lt;i&gt;et al.&lt;/i&gt; developed the multistate continuum theory for multiple charge reactions and deduced the rate expressions for nonadiabatic PCET reactions in solution, laying the theoretical foundation for the analysis of PCET kinetics in electrochemical processes. In 2006, Saveant &lt;i&gt;et al.&lt;/i&gt; verified the concerted proton and electron transfer (CPET) mechanism in the oxidation of phenols coupled with intramolecular amine-driven proton transfer (PT). Their subsequent work in 2008 reported the pH-dependent pathways of electrochemical oxidation of phenols.&lt;/p&gt;\u0000 \u0000 &lt;p&gt;Electrolyte effects in electrocatalysis have gained emphasis in recent years. In 2009, Markovic's pioneering work proposed non-covalent interactions between hydrated alkaline cations and adsorbed OH species in oxygen reduction reaction (ORR)/hydrogen oxidation reaction (HOR). In 2011, Markovic &lt;i&gt;et al.&lt;/i&gt; significantly enhanced hydrogen evolution reaction (HER) activity in alkaline solution by improving water dissociation, which was assumed to dominate the sluggish HER kinetics in such media. In comparation, Yan &lt;i&gt;et al.&lt;/i&gt; applied hydrogen binding energy (HBE) theory in 2015 to explain the pH-dependent HER/HOR activity. Cations play a significant role in regulating the selectivity and activity of carbon dioxide reduction (CO&lt;sub&gt;2&lt;/sub&gt;RR). In 2016 a","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3533-3552"},"PeriodicalIF":5.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641233","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}

{"title":"Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters†","authors":"Yu-Shen Zhu,&nbsp;Jia-Xin Li,&nbsp;Hao-Tian Zhao,&nbsp;Bo Su","doi":"10.1002/cjoc.202400700","DOIUrl":"https://doi.org/10.1002/cjoc.202400700","url":null,"abstract":"<div>\u0000 \u0000 \u0000 <section>\u0000 \u0000 <p>Vicinal stereogenic centers are ubiquitous structural scaffolds in both natural products and synthetic compounds, yet their enantioselective construction remains a significant challenge in organic synthesis. Organoboron compounds are of paramount importance in synthetic chemistry due to their ability to undergo facile transformations, yielding diverse essential chemical bonds such as carbon-carbon, carbon-oxygen, carbon-nitrogen, and carbon-halogen bonds. Transition-metal-catalyzed asymmetric borylative functionalizations of internal alkenes offer a promising strategy for the enantioselective installation of two adjacent chiral centers across carbon-carbon bonds. By leveraging the versatile transformations of the newly introduced boryl unit, this approach holds great potential for expanding the structural diversity of vicinal stereogenic scaffolds. In this concise review, we aim to highlight recent advancements in transition-metal-catalyzed asymmetric borylative functionalizations of internal alkenes, underscore their utility as a versatile approach for constructing vicinal stereogenic centers, and discuss unsolved challenges and future directions in this field.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p></p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3588-3604"},"PeriodicalIF":5.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641230","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}

{"title":"Regulatory Mechanisms and Applications of Rare Earth Elements-Based Electrocatalysts†","authors":"Qinlong Gao,&nbsp;Haoyuan Wang,&nbsp;Chunxiao Liu,&nbsp;Laihao Luo,&nbsp;Xu Li,&nbsp;Qiu jiang,&nbsp;Yuan Ji,&nbsp;Tingting Zheng,&nbsp;Chuan Xia","doi":"10.1002/cjoc.202400578","DOIUrl":"https://doi.org/10.1002/cjoc.202400578","url":null,"abstract":"<div>\u0000 \u0000 \u0000 <section>\u0000 \u0000 <p>Amidst the pressing environmental challenges posed by the prevalent reliance on fossil fuels, it becomes imperative to seek sustainable alternatives and prioritize energy efficiency. Electrocatalysis, which is renowned for its high efficiency and environmental friendliness, has garnered significant attention. Rare earth elements (REEs), distinguished by their unique electronic and orbital structures, play a crucial role in electrocatalysis. The strategic integration of REEs into catalysts allows for the fine-tuning of atomic structures, which in turn, significantly boosts catalytic performance. Despite substantial advancements in rare earth-based materials for electrocatalysis, a comprehensive overview of the regulatory mechanisms involving REEs is lacking. In this mini-review, we systematically explore the regulatory mechanisms of REEs within electrocatalysts and their pivotal roles in essential electrocatalytic processes such as the CO₂ reduction reaction, oxygen reduction reaction, and hydrogen evolution reaction. We commence with an elucidation of REEs, proceed to delineate their regulatory impacts on electrocatalysts and delve into their applications in key electroreduction reactions. We conclude with discussions on current limitations and prospects for further advancements in this burgeoning field of research.\u0000\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p></p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"205-218"},"PeriodicalIF":5.5,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142869159","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}

{"title":"Recent Advances of Boron-Containing Chiral Luminescent Materials†","authors":"Jiaqi Di,&nbsp;Shuran Han,&nbsp;Pangkuan Chen","doi":"10.1002/cjoc.202400843","DOIUrl":"https://doi.org/10.1002/cjoc.202400843","url":null,"abstract":"<div>\u0000 \u0000 <section>\u0000 \u0000 <h3> Comprehensive Summary</h3>\u0000 \u0000 <p>As a class of organic dyes, boron-containing compounds play an important role in organic luminescent materials. They have attracted considerable attention due to their unique photophysical properties. Chiral luminescent systems have a wide range of practical applications in biological imaging, optoelectronic devices, information storage and 3D display. Boron-containing chiral luminescent materials can not only effectively improve the luminescent properties of CPL materials, but also bring unique properties to the system, which enables them to be used as favorable CPL emitting materials for an expanded range of applications. Here, we review the research progress of boron-containing chiral luminescent materials by the detailed discuss according to different chiral skeletons, such as point chirality, 1,1’-binaphthyl, [<i>n</i>]helicenes, [2,2]paracyclophane and pillar[5]arenes. We believe that this review is of significance for the development of boron-containing compounds and CPL materials.\u0000\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p>The studies of circularly polarized luminescence (CPL) based on small organic molecules have advanced significantly. However, boron-containing chiral luminescent materials have gained attention only in recent years. In 2019, Zhao's group prepared a binaphthalene derivative modified with triarylborane, representing the organic small molecule luminescent material to exhibit CPL characteristics responsive to both solvent and fluoride ions. In 2020, the Chen's group used the unique luminescence properties and steric effects of triarylborane and triphenylamine to prepare CPL materials based on the planar chiral pillar[5]arenes. In 2021, Wang's group developed a new class of B,N-embedded double hetero[7]helicenes molecules that exhibit strong chiroptical responses in the UV-visible region. In the same year, He's group used asymmetric reactions to synthesize boron-based point-chirality compounds with high efficiency and enantioselectivity. In 2023, Ravat synthesized 1,4-B,N-embedded helicenes exhibiting narrow-band fluorescence and CPL. During this period, Matthias Wagner <i>et al</i> obtained (BO)₂-doped tetrathia[7]helicene via an efficient four-step synthesis, and Zheng reported the nearly pure green circularly polarized electroluminescent device (CP-OLED). In 2024, Chen's group prepared B,N-embedded hetero-[9]helicenes offering a pathway towards significantly enhanced efficiency in helicene-based CPEL.\u0000\u0000 </p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"219-238"},"PeriodicalIF":5.5,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142869160","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}

{"title":"Recent Advances in Methodologies for Radical-Mechanistic Borylation†","authors":"Chang Lian,&nbsp;Jianning Zhang,&nbsp;Di Qiu,&nbsp;Fanyang Mo","doi":"10.1002/cjoc.202400694","DOIUrl":"https://doi.org/10.1002/cjoc.202400694","url":null,"abstract":"<div>\u0000 \u0000 \u0000 <section>\u0000 \u0000 <p>We reviewed works on radical borylation reactions since 2020 from two aspects. <b>1. Borylation from alkyl or aryl radicals</b>: This approach involves the generation of alkyl or aryl radicals from various precursors such as halides and carboxylic acids, followed by their reaction with diboron reagents to form boron esters. <b>2. Borylation from boron-centered radicals</b>: This approach involves generating boron-centered radicals, which then react with substrates to achieve borylation.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p></p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"104-115"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142759839","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}

{"title":"Ytterbium-Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes","authors":"Bin Chen,&nbsp;Shan Zhong,&nbsp;Huilin Zhan,&nbsp;Zhangyu Han,&nbsp;Jianwei Sun,&nbsp;Hai Huang","doi":"10.1002/cjoc.202400874","DOIUrl":"https://doi.org/10.1002/cjoc.202400874","url":null,"abstract":"<div>\u0000 \u0000 <p>A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of <i>N</i>-allenamides (or aryloxyallenes) with 3-alkoxycarbonyl-2-pyrones has been developed for the efficient synthesis of diarylmethanes with moderate to good yields. The reaction exhibits good functional group tolerance and can be applied to late-stage modifications of known drug molecules. Mechanistic studies indicate that the ester group at the 3-position of 2-pyrones is essential, and the initial Diels–Alder reaction between the 2-pyrones and the proximal C=C bond of the <i>N</i>-allenamides (or aryloxyallenes) is crucial for the success of the reaction.</p>\u0000 <p></p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"199-204"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142868552","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}