Chinese Journal of Chemistry最新文献

{"title":"Asymmetric Synthesis of Chiral Aliphatic α-Tertiary Aminonitriles via Organocatalytic Isomerization of Cyanoketimines","authors":"Ling Xu,&nbsp;Jisheng Luo,&nbsp;Li Deng","doi":"10.1002/cjoc.202400774","DOIUrl":"https://doi.org/10.1002/cjoc.202400774","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral <i>α</i>-tertiary aminonitriles are valuable synthetic intermediates. They are also found in various structures of biologically active molecules. Therefore, numerous reports of catalytic asymmetric synthesis of chiral <i>α</i>-aminonitriles continuously emerged during the past few decades. Great strides have been made for the synthesis of chiral <i>α</i>-aryl and <i>α</i>-branched alkyl aminonitriles. However, efficient methods for catalytic asymmetric synthesis of chiral <i>α</i>-linear alkyl aminonitriles remain limited. We herein report a new synthetic approach to chiral <i>α</i>-tertiary alkyl aminonitriles via catalytic asymmetric isomerization of cyanoketimines. The synthetic value of this method was illustrated by application to a concise catalytic asymmetric synthesis of vildagliptin.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3387-3392"},"PeriodicalIF":5.5,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642408","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":"Tuning Hydrophilic Segments to Achieve Acid-Free Proton Conduction in COF","authors":"Kun Zhang,&nbsp;Lei Wu,&nbsp;Yanting Zhang,&nbsp;Hong Zhang,&nbsp;Dongshuang Wu","doi":"10.1002/cjoc.202400704","DOIUrl":"https://doi.org/10.1002/cjoc.202400704","url":null,"abstract":"<div>\u0000 \u0000 <p><b>R</b>apid dynamics and remarkable proton conduction induced by c<b>onfined water</b> in nanospaces have attracted much attentions from researchers, which is crucial for advancing the development of innovative proton conductors and deepening comprehension of proton and water transport mechanisms within biological systems. In this aspect, carbon nanotubes (CNTs) are frequently employed as a research platform. However, they possess certain limitations, such as their inherent electronic conductivity and extreme hydrophobicity, which can impede the accurate assessment and precise regulation of proton conduction. We herein prepared two 2D COFs with different hydrophilic fragment, and obtained maximum acid-free proton conductivity of 3.04 × 10^–4 S·cm^–1 at 70 °C and 100% RH with Grotthuss type activation energy of 0.14 eV. This is mainly due to that the water molecules in the center of channel form strong hydrogen bonds, enhancing proton dissociation and guiding fast directional diffusion.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"61-66"},"PeriodicalIF":5.5,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142762635","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":"Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp3)–H Feedstocks via C(sp3)–H/C(sp2)–H Functionalization","authors":"Jing Yuan,&nbsp;Jiao Zhou,&nbsp;Peng-Fei Xia,&nbsp;Yu Liu,&nbsp;Ke-Wen Tang,&nbsp;Jian-Hong Fan","doi":"10.1002/cjoc.202400748","DOIUrl":"10.1002/cjoc.202400748","url":null,"abstract":"<div>\u0000 \u0000 <p>The difunctionalization of bicyclo[1.1.0]butanes is an under-explored transformation that accesses to moieties that are otherwise difficult to prepare. Herein, a new oxidative radical alkylarylation of <i>N</i>-aryl bicyclobutyl amides with C(sp³)−H feedstocks is achieved in an atom-economic and photocatalyst- and light-free manner. This protocol follows a sequential C(sp³)–H/C(sp²)–H functionalization, providing an efficient route for diversity-oriented synthesis of functionalized 3-spirocyclobutyl oxindoles. In particular, a wide range of C(sp³)−H feedstocks, including ether, alcohol, amine, thioether, polychlorinated methane, silane, acetone, acetonitrile, toluene, and alkane are all suitable for the C(sp³)−H functionalization, demonstrating the broad applicability of this transformation.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3399-3404"},"PeriodicalIF":5.5,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269630","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":"Highly Stable Binary Cross-Linkable Organic Nonlinear Optical Materials Using Different Acceptors Based on Huisgen Cycloaddition Reaction","authors":"Yu Zhang,&nbsp;Weijun Zhang,&nbsp;Shuhui Bo,&nbsp;Wenlong He,&nbsp;Chuying Liu,&nbsp;Jiahai Wang,&nbsp;Fenggang Liu","doi":"10.1002/cjoc.202400711","DOIUrl":"10.1002/cjoc.202400711","url":null,"abstract":"<div>\u0000 \u0000 <p>How to obtain organic electro-optic materials with large electro-optic coefficients, high glass transition temperature, and good optical transparency remains a challenge in this field. To solve this problem, we introduce groups that can undergo Huisgen cycloaddition reactions into the donor and electron bridge of chromophores with large hyperpolarizability using tetrahydroquinoline as the donor. Binary cross-linkable chromophores TLD1-2 with CF₃-TCF as the acceptor and chromophores TLD3-4 with 5Fph-TCF as the acceptor were synthesized. After poling and crosslinking, the <i>T</i>_g of TLD1/TLD2 and TLD3/TLD4 were raised to 152 and 174 °C, respectively. The electro-optical coefficients of chromophores TLD1/TLD2 and TLD3/TLD4 were as high as 312 pm/V and 287 pm/V, respectively. The long-term alignment stability test showed that after being left at 85 °C for 500 h, the cross-linked film TLD3/TLD4 can still maintain more than 98% of the original electro-optical coefficient value, which is higher than that of TLD1/TLD2 (93%). The chromophore TLD3-4 exhibited much blue-shifted maximum absorption wavelengths (~40 nm) compared to TLD1-2 which was beneficial for reducing optical loss in the device. The combination of high electro-optic coefficient, strong stability, and excellent optical transparency makes the TLD series of binary cross-linked materials very promising for practical high-performance electro-optic devices.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3219-3226"},"PeriodicalIF":5.5,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269925","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":"Reduction of Tertiary Carbon Radicals via Asymmetric Hydrogen Atom Transfer (AHAT)†","authors":"Xue Han,&nbsp;Chuan He","doi":"10.1002/cjoc.202400296","DOIUrl":"10.1002/cjoc.202400296","url":null,"abstract":"<div>\u0000 \u0000 <section>\u0000 \u0000 <h3> Comprehensive Summary</h3>\u0000 \u0000 <p>In the past two decades, the development of asymmetric radical reactions has achieved tremendous progress, which has emerged as a powerful tool for the synthesis of chiral molecules in synthetic chemistry. Among the diverse array of radical processes, the transfer of hydrogen atoms to tertiary carbon radicals offers the potential for constructing chiral tertiary carbon centers in a stereoselective fashion. Notwithstanding the challenges associated with the reactive and evanescent nature of radical species, the use of chiral reagents or mediators has enabled the stereocontrol of the asymmetric hydrogen atom transfer (<b>AHAT</b>), which provides novel avenues for advancing the field of asymmetric synthesis.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3414-3428"},"PeriodicalIF":5.5,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266906","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":"Epitaxially Growing 2D RGB Trichromatic Cocrystal Nanomeshes to Trigger Cross-Modulation White Light Emission","authors":"Wenyubin Luo,&nbsp;Cheng Zhang,&nbsp;Shan Yang,&nbsp;Lei Ding,&nbsp;Yang Li,&nbsp;Yanqiu Sun,&nbsp;Qichun Zhang","doi":"10.1002/cjoc.202400687","DOIUrl":"10.1002/cjoc.202400687","url":null,"abstract":"<div>\u0000 \u0000 <p>Considering their oriented crystalline structure and high luminescent efficiency, the exploration of multi-component organic cocrystal systems with tunable supramolecular nanostructures and potential RGB light emission has emerged as a captivating but challenging subject. Here, we propose a straightforward synthetic strategy to precisely govern the assembly, structure and structure-property relationship of organic cocrystals. By employing the single-crystalline template-assisted epitaxial growth (SCT-EG) method, the two-dimensional (2D) highly-aligned cocrystal nanomeshes are firstly developed to afford an exceptional RGB trichromatic system, triggering cross-modulation white light emission (WLE) with remarkable stability and regeneration capacity over six months. The transformation from random 1D microstructures to uniformly-oriented 2D nanomeshes can be attributed to the regulatory competitive intermolecular π-π, CT interactions, and partial H bond interactions among cocrystals. Moreover, the successful construction of 2D RGB trichromatic cocrystal nanomeshes system holds promise to generate full-color display, which can function as multicolor inks for photonic dynamic recognition, information encryption, and decryption.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3379-3386"},"PeriodicalIF":5.5,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266907","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":"Decarboxylative and Decarbonylative Borylation of Carboxylic Acids and Their Derivatives†","authors":"Xiaoxian Li,&nbsp;Lipeng Wu","doi":"10.1002/cjoc.202400616","DOIUrl":"10.1002/cjoc.202400616","url":null,"abstract":"<div>\u0000 \u0000 <section>\u0000 \u0000 <h3> Comprehensive Summary</h3>\u0000 \u0000 <p>Boronate esters are highly valued in synthetic and pharmaceutical industries for their versatility in creating C—C and C—X bonds. They also find applications as catalysts in chemical transformations as well as stimuli-responsive materials in materials science. Some alkyl boronates themselves also show promising applications in medicinal chemistry. In the past few decades, chemists have been devoted to developing new methods or new starting materials for synthesizing boronate esters. Carboxylic acids and their derivatives are privileged chemical entities due to their readily availability or natural abundance, structural diversity, and chemical stability. Hence, the transformation of carboxylic acid and their derivatives to alkyl/aryl boronate esters has seen its fast development in the past decade. This review summarized the state-to-art development of decarboxylative and decarbonylative borylation of carboxylic acids and their derivatives to aryl and alkyl boronate esters.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p>The decarboxylative and decarbonylative borylation of carboxylic acids and their derivatives started only in the past decade. In 2016, the decarbonylative borylation of carboxylic esters and amides was reported by Zhuangzhi Shi and Magnus Reuping's groups. Then, in 2017, studies on the decarboxylative borylation of redox-active esters such as NHPI esters started to receive increasing attention by Aggarwal, Baran, Fu, Glorius, and Li's groups. From 2018 to 2023, large numbers of studies on the decarboxylative and decarbonylative borylation of carboxylic acids and their derivatives using transition-metal-catalyst, organo-catalyst, or under photochemical or electrochemical conditions emerged. Due to space limitations, only pictures of scientists who have contributed more than two works in this area are shown herein.\u0000 </p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3429-3440"},"PeriodicalIF":5.5,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266873","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":"Eutypetides A—E, Structurally Intriguing Polyketides Formed by Intramolecular [4+2] Cycloaddition from Marine-Derived Fungus Eutypella sp. F0219","authors":"Zhong-Ping Jiang,&nbsp;Meng-Ting Chen,&nbsp;Xiao Xiang,&nbsp;Cong-Jun Xu,&nbsp;Yong Rao,&nbsp;Hong-Zhi Du,&nbsp;Wan-Shan Li,&nbsp;Ling Huang","doi":"10.1002/cjoc.202400716","DOIUrl":"10.1002/cjoc.202400716","url":null,"abstract":"<div>\u0000 \u0000 <p>Four polycyclic ten-membered lactones possessing unprecedented 10/6/5 tricyclic ring skeleton, named eutypetides A—D (<b>1</b>—<b>4</b>), and an intriguing polyketide containing a hexahydroisobenzofuran-1(3<i>H</i>)-one motif, named eutypetide E (<b>5</b>) were isolated from the marine-derived fungus <i>Eutypella</i> sp. F0219, together with three new related biosynthetic polyketides eutypetides F—H (<b>6</b>—<b>8</b>). The absolute configurations of <b>1</b>—<b>5</b> were unequivocally determined by single-crystal X-ray diffraction analyses (Cu Kα), modified Mosher's method and electronic circular dichroism (ECD) calculations. Eutypetides G (<b>7</b>) showed remarkable anti-inflammatory activity and could reduce the mRNA expression of proinflammatory cytokines IL-1β, IL-6, TNF-α, and iNOS induced by LPS. Most notably, compounds <b>1</b>—<b>4</b> were formed biogenetically from <b>6</b>—<b>7</b> via the key intramolecular [4+2] cycloaddition, while compound <b>5</b> could be constructed biogenetically from <b>8</b> through the intramolecular [4+2] cycloaddition. All the above eight polyketides are proposed to originate from a C₁₀ and a C₆ fatty acid.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"23-32"},"PeriodicalIF":5.5,"publicationDate":"2024-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266875","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":"A Dinitrogen Divanadium Complex Supported by a Trisamidophosphine Ligand","authors":"Dong-Ping Chen,&nbsp;Yun-Shu Cui,&nbsp;Bo-Han He,&nbsp;Feng Liu,&nbsp;Dan-Dan Zhai,&nbsp;Zhang-Jie Shi","doi":"10.1002/cjoc.202400693","DOIUrl":"10.1002/cjoc.202400693","url":null,"abstract":"<div>\u0000 \u0000 <p>The reaction between tripodal trisamidophosphine ligand H₃PN₃^Ar and V(Mes)₃(THF) (Mes = mesityl) yields the vanadium(III) complex (PN₃^Ar)V (<b>1</b>) with an open site in the axial position, which could coordinate with THF, pyridine, and NH₃ to form the corresponding adducts (<b>2</b>—<b>4</b>). The vanadium(III) center is redox-active, as demonstrated by cyclic voltammetry methods and chemical oxidation or reduction. Notably, a novel dinitrogen divanadium complex with a bridging N₂ ligand, {K(THF)}₂{[PN₃^Ar]V}₂(<i>μ</i>-N₂) (<b>6</b>), was synthesized via treatment of <b>1</b> with 1 equivalent of potassium naphthalenide in THF under a N₂ atmosphere. The electronic structures and binding properties of <b>6</b> are evaluated and discussed based on its DFT calculations. Additionally, these vanadium complexes (<b>1</b>, <b>5</b>, <b>6</b>) can serve as catalysts for the conversion of N₂ into N(SiMe₃)₃ in the presence of reductants and Me₃SiCl.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"39-45"},"PeriodicalIF":5.5,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266910","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":"Synthesis of Indole-Fused Eight-Membered Oxa-Rings via Palladium-Catalyzed Asymmetric [4+4] Cycloaddition of Indole-2,3-Quinodimethanes with 2-Alkylidenetrimethylene Carbonates","authors":"Xinhao Lu,&nbsp;Yi Wang,&nbsp;Chenghan He,&nbsp;Yang-Zi Liu,&nbsp;Wei-Ping Deng","doi":"10.1002/cjoc.202400764","DOIUrl":"10.1002/cjoc.202400764","url":null,"abstract":"<div>\u0000 \u0000 <p>We report a palladium-catalyzed asymmetric [4+4] cycloaddition reaction between 2-alkylidenetrimethylene carbonate and electron-deficient indole-2,3-quinodimethanes (<b>IQDMs</b>). This reaction features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity (up to 95% ee), and easy scale-up without any loss of efficiency, making it valuable for the synthesis of indole-fused eight-membered oxa-rings.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3393-3398"},"PeriodicalIF":5.5,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266874","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}