Chinese Journal of Chemistry最新文献

{"title":"Selective and Scalable Deuteration of Heteroarenes Using Nickel-Based Nanoparticles†","authors":"Feiyu Qiu,&nbsp;Lingyun Yang,&nbsp;Yuan Gao,&nbsp;Jiapei Yang,&nbsp;Aiwen Lei,&nbsp;Wu Li","doi":"10.1002/cjoc.202300644","DOIUrl":"10.1002/cjoc.202300644","url":null,"abstract":"<div>\u0000 \u0000 <p>Deuterium labelling possesses wide applications in pharmaceuticals, chemical science and materials science. Development of efficient methodologies for the synthesis of deuterium labelled compounds, especially hydrogen isotope exchange (HIE), continued to receive an impressive attention over the years. Herein, we developed a nitrogen doped nano-scale nickel catalyst for deuterium incorporation of a variety of nitrogen heterocycles using D₂O as the isotope source. The usefulness of this approach has been demonstrated by 10 g-scale for complex pharmaceuticals. This methodology represents a practical and scalable deuteration and the air- and water-stable nanocatalyst enables efficient labelling in a straightforward manner.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2993-2998"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227737","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":"Modular, Scalable Total Synthesis of Neopetromin†","authors":"Hiroshige Ogawa,&nbsp;Yuuya Nagata,&nbsp;Hugh Nakamura","doi":"10.1002/cjoc.202400637","DOIUrl":"10.1002/cjoc.202400637","url":null,"abstract":"<p>The first total synthesis of neopetromin, featuring the highly strained Tyr C-6-to-Trp N-1’ linkage, is hereby reported. This modular synthetic strategy, employing C—H arylation and Larock macrocyclization, offers a novel approach to the synthesis of various RiPPs natural product families.</p><p>\u0000 </p>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3023-3028"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cjoc.202400637","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195527","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":"Stereoselective Synthesis of C-Vinyl Glycosides via Nickel-Catalyzed Cross-Electrophile Couplings of 1,2-Glycosyl Orthoesters and Vinyl Halides","authors":"Xin Wang,&nbsp;Anrong Chen,&nbsp;Shiyin Zhao,&nbsp;Qiang Tao,&nbsp;Bo Yang,&nbsp;Xing Zhang,&nbsp;Feng Zhu","doi":"10.1002/cjoc.202400651","DOIUrl":"10.1002/cjoc.202400651","url":null,"abstract":"<div>\u0000 \u0000 <p>A highly stereoselective nickel-catalyzed cross-electrophile coupling of readily accessible, novel, stable oxygen-based glycosyl radical precursors, specifically 1,2-glycosyl orthoesters, is developed. This approach offers an effective pathway to synthesize diverse <i>C</i>-vinyl glycosides, characterized by good yields, excellent stereoselectivity, mild reaction conditions, a broad substrate scope, and versatile transformations of the resulting products.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3029-3034"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195607","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":"Pressure-Triggered Photochromism in Chiral Salicylaldehyde Schiff Bases","authors":"Yajing Li,&nbsp;Jiacong Fu,&nbsp;Bohan Yao,&nbsp;Pengyu Zeng,&nbsp;Qiuchen Peng,&nbsp;Yuanyuan Li,&nbsp;Kai Li,&nbsp;Shuangquan Zang","doi":"10.1002/cjoc.202400541","DOIUrl":"10.1002/cjoc.202400541","url":null,"abstract":"<div>\u0000 \u0000 <p>Salicylaldehyde Schiff base is a kind of important photochromism system, whose photochromism process is widely acknowledged to be co-determined by the electronic structure and molecular conformation. Normally, salicylaldehyde Schiff base derivatives with α-type structures tend to exhibit photochromism while those with β-type structures tend to be photostable. However, more and more counterexamples are found, and the root cause of photochromism property of salicylaldehyde Schiff base is still unclear. In this work, a series of chiral salicylaldehyde Schiff bases and their racemates were prepared. The formers are photochromic while the latters are photostable. Influenced by Wallach's rule, the homochiral counterparts have looser packing modes than that of the racemic counterparts. Mechanism study revealed that the pressure should be the root cause of photochromism property. Close molecule packing can restrict the photochromism property effectively after being pressed, which also explains why the photochromism of salicylaldehyde Schiff base is usually observed in solid state. This work not only reports the unique photo-responsive difference between the chiral salicylaldehyde Schiff bases and their racemates, more importantly, provides a new perspective to understand the influence of molecule pressure on their photophysical properties.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2987-2992"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195542","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":"Palladium-Catalyzed Construction of Phthalides Bearing Two Adjacent Stereocenters through Retro-oxa-Michael Addition","authors":"Li-Xia Liu,&nbsp;Tong Niu,&nbsp;Yu-Qing Bai,&nbsp;Yong-Gui Zhou","doi":"10.1002/cjoc.202400612","DOIUrl":"10.1002/cjoc.202400612","url":null,"abstract":"<div>\u0000 \u0000 <p>Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium-catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo-, enantio- and diastereoselectivity. Furthermore, gram-scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3006-3012"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195525","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":"Rational Design of Co(II)-Pyridine-Decorated Reduced Phosphomolybdate Photocatalysts for Efficient Aniline Oxidation under Mild Conditions","authors":"Xiaohui Liu,&nbsp;Hui Li,&nbsp;Na Xu,&nbsp;Yanyan Guo,&nbsp;Xiaoyan Zhang,&nbsp;Xiuli Wang","doi":"10.1002/cjoc.202400642","DOIUrl":"10.1002/cjoc.202400642","url":null,"abstract":"<div>\u0000 \u0000 <p>The conversion of aniline to nitrosobenzene (NSB), a key step in the synthesis of important chemicals, demands the development of environmentally friendly photocatalysts that operate under mild conditions. This process is driven by the need for sustainable methods, given toxic nature of aniline and its central role in the production of dyes, pharmaceuticals, and agricultural chemicals. This study reports on the synthesis of three reduced phosphomolybdate compounds with Co(II) centers and polypyridine ligands, which show great potential as photocatalysts for the mild oxidation of aniline to NSB. The synthesis uses 30% H₂O₂ as the oxidant and the compounds as the sole catalysts, achieving high conversion rates and selectivity without additional additives or photosensitizers. The integration of multidentate ligands with {P₄Mo₆} clusters significantly reduces the band gap, facilitating visible-light-driven photocatalysis. The adsorption interaction between coordinated water molecules and Co ions and H₂O₂ is found to enhance the conversion rate of aniline, a finding supported by DFT analyses.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2970-2978"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142225163","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":"Enhanced One/Two-Photon Initiating Performance of Nitro-Carbazole-Styrene Based Oxime/Ketoxime Esters","authors":"Jie Xie,&nbsp;Yonghui Wang,&nbsp;Xiaobin Wang,&nbsp;Xuefeng Fang,&nbsp;Qinyan Zhu,&nbsp;Chun Cao,&nbsp;Ming Jin","doi":"10.1002/cjoc.202400629","DOIUrl":"10.1002/cjoc.202400629","url":null,"abstract":"<div>\u0000 \u0000 <p>Photoinitiators of the oxime ester (OXE) or ketoxime ester (OXE-CO) type can rapidly undergo N—O bond cleavage and generate free radicals to initiate photopolymerization under LED excitation, occupying an important position in the field of photocuring. However, the commercial OXEs, <i>e.g</i>., OXE 01 and 02 with <i>λ</i>_max's at 326 and 344 nm, respectively, still do not well match the emission spectra of LEDs. Developing novel OXEs/OXE-COs with high photosensitivity for long-wavelength LEDs has great significance. Here, four new OXEs/OXE-COs with nitro-carbazole-styrene conjugated chromophore were designed, synthesized, and used as photoinitiators. Results demonstrated that all photoinitiators had strong absorption within the UV–vis range (<i>λ</i>_max: 381—392 nm, ε_max: 8200—11500 M⁻¹·cm⁻¹). Molecular design of the oxime ester cleavage to produce a small volume methyl group and a methacryl group with an unsaturated double bond brings high activity and low migration, respectively, in one-photon polymerization under 365—450 nm LEDs excitation. Moreover, OXEs/OXE-COs with PETA exhibited a wide processing window, high resolution (line accuracy~100 nm) and good nano-patterning capability under 780 nm femtosecond laser irradiation in two-photon polymerization, indicating their great potential in 2D/3D microfabrication technologies.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3013-3022"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195524","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":"Ultrathin PdAu Nanowires with High Alloying Degree for the Direct Oxidation of Methane to C1 Oxygenates","authors":"Linhui Tan,&nbsp;Yi Shi,&nbsp;Yueshan Xu,&nbsp;Xue Zhang,&nbsp;Daoxiong Wu,&nbsp;Zhitong Wang,&nbsp;Juanxiu Xiao,&nbsp;Huan Wen,&nbsp;Jing Li,&nbsp;Xinlong Tian,&nbsp;Peilin Deng","doi":"10.1002/cjoc.202400591","DOIUrl":"10.1002/cjoc.202400591","url":null,"abstract":"<div>\u0000 \u0000 <p>The direct oxidation of methane (CH₄) into high-valued C1 oxygenates production has garnered increased attention in effectively using vast CH₄ and alleviating the global energy crisis. However, due to the high cleavage energy of C—H bond and low polarity of CH₄ molecule, it is difficult to activate the first C—H bond. Furthermore, C1 oxygenates are readily inclined to be oxidized to CO₂, because their weaker C—H bond comparing with CH₄ molecule, resulting in poor selectivity. Herein, we designed ultrathin Pd_<i>x</i>Au_<i>y</i> alloy NWs supported on ZSM-5 (Z-5) to investigate the direct oxidation of CH₄ to high value-added oxygenate under mild conditions. By precisely adjusting the molar ratio of Pd/Au and alloying degree, Pd₉Au₁NWs/Z-5 showed an excellent yield of 11.57 mmol·g^–l·h^–1 and the outstanding selectivity of 95.1% for C1 oxygenates (CH₃OH, CH₃OOH and HCOOH). The <i>in-situ</i> spectroscopic and mechanism analysis proved that the enhanced catalytic performance of Pd₉Au₁NWs/Z-5 was ascribed to the stable one-dimensional nanostructure and the strong synergy effect with high alloying PdAu, which could increase the adsorption capacity of CH₄ molecules on Pd atoms to promote the CH₄ conversion. This work offers valuable insights into the design concept of high-efficient catalysts and the structure-activity relationship for the direct oxidation of CH₄.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2999-3005"},"PeriodicalIF":5.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195526","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.202490182","DOIUrl":"https://doi.org/10.1002/cjoc.202490182","url":null,"abstract":"<p>3,4-Dihydroquinazoline frameworks which have frequently been encountered in natural products and bioactive molecules, prompted the development of creative pharmaceuticals owing to their prominent biological properties, such as trypanothione reductase inhibitor, Hepatitis B virus inhibitive activities, anticancer activities, <i>etc</i>. <i>De novo</i> assembling of chiral 3,4-dihydroquinazolines from simple chemical feedstocks via multicomponent reactions remains several great obstacles, and this scenario is capable of the divergent and flexible modulation of these skeletons which is urgently required for drug discovery. More details are discussed in the article by Yu <i>et al</i>. on page 2140—2146.\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 18","pages":"2122"},"PeriodicalIF":5.5,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cjoc.202490182","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986040","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":"Earth-Abundant Nickel-Catalyzed Asymmetric Hydrogenation†","authors":"Peng Wang,&nbsp;Zhao-Lin He,&nbsp;Zi-Fei Xia,&nbsp;Jun Wei,&nbsp;Xiu-Qin Dong","doi":"10.1002/cjoc.202400352","DOIUrl":"10.1002/cjoc.202400352","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;Transition metal-catalyzed asymmetric hydrogenation is an efficient and direct synthetic method to access chiral compounds, which features simplicity, easy working-up process, and high atomic economy. It typically relies on precious transition metal catalytic systems, including ruthenium, rhodium, iridium and palladium, which always face the difficulties of limited resources, high cost, and environmental contamination. Therefore, great efforts were made to apply earth-abundant, low (non-)toxic, and environmentally friendly transition metals, such as iron, cobalt, nickel and copper, to the asymmetric hydrogenation in the past decades, and some considerable breakthroughs have been obtained. In this review, we mainly summarized some recent research progress of nickel-catalyzed asymmetric hydrogenation of prochiral unsaturated molecules, including olefins, imines and ketones. And continuous development of chiral nickel catalytic systems and the application of them into challenging asymmetric hydrogenation is prospected in the future.&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;Transition metal-catalyzed asymmetric hydrogenation has been regarded as an important and direct approach to access chiral molecules. The first example of homogeneous catalytic asymmetric hydrogenation was developed by Knowles and Horner in 1968, respectively. In 1971, Kagan developed privileged chiral DIOP ligand for asymmetric hydrogenation. Halpern and Brown made deep studies on the Rh-catalyzed asymmetric hydrogenation in 1977, respectively. Noyori developed a powerful and privileged chiral BINAP ligand in 1980. Owing to Knowles and Noyori's great contribution in the field of catalytic asymmetric hydrogenation, they were awarded the Nobel Prize in Chemistry in 2001. In 1984, Ohkubo developed pioneering earth-abundant transition metal Ni-catalyzed asymmetric hydrogenation of ethyl α-methylcrotonate. A great many scientists made tremendous contribution to the development of chiral privileged ligands, such as, Bosnich, Kumada, Giongo, Takaya, Miyashima, Achiwa, Burk, Pflaltz, Chan, X. Zhang, Imamoto, Zhou, Genet, Sannicolo, Ding, Hoge, W. Zhang, Z. Zhang, Tang, these ligands owned wide application in the catalytic asymmetric hydrogenation. In addition, Zhou, Fan made deep investigation on the asymmetric hydrogenation of challenging aromatic heterocyclic compounds. Owing to the great importance of the development of the asymmetric (transfer) hydrogenation promoted by cheap transition metal catalytic systems, some researchers, such as Hamada, Gao, J. S. Zhou, Chirik, X. Zhang, Y.-G. Zhou, W. Zhang, Lv, Dong, Fu, Deng, and Hou, made great efforts to the development of earth-abundant nickel-catalyzed asymmetric hydrogenation o","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3135-3156"},"PeriodicalIF":5.5,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195543","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}