Xinhao Lu, Yi Wang, Chenghan He, Yang-Zi Liu, Wei-Ping Deng
{"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, Yi Wang, Chenghan He, Yang-Zi Liu, 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}
Jiarong Peng, Tianhui Hao, Wenjing Ma, Zhuojia Xu, Tiehai Li
{"title":"Chemoenzymatic Synthesis of Common Legionaminic Acid−Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44†","authors":"Jiarong Peng, Tianhui Hao, Wenjing Ma, Zhuojia Xu, Tiehai Li","doi":"10.1002/cjoc.202400794","DOIUrl":"https://doi.org/10.1002/cjoc.202400794","url":null,"abstract":"<i>Acinetobacter baumannii</i> infections pose a great threat to public health owing to upsurging antibiotic resistance. Capsular polysaccharides (CPS) are major virulence determinants of pathogenic bacteria and have attracted much attention as potential targets for vaccine development. However, the obtainability of structurally well-defined CPS-related oligosaccharides remains challenging. Herein, we report an efficient chemoenzymatic strategy for the first total synthesis of common CPS pentasaccharide repeating unit of <i>Acinetobacter baumannii</i> K27 and K44, containing a difficult-to-construct α-linked 5,7-di-<i>N</i>-acetyllegionaminic acid (Leg5,7Ac<sub>2</sub>) residue. The chemical synthesis of a branched tetrasaccharide precursor was accomplished by flexible orthogonal protecting-group manipulations and stereocontrolled glycosylations. Furthermore, the enzyme-catalyzed stereoselective installment of legionaminic acid residue into the tetrasaccharide, using one-pot multienzyme (OPME) synthesis system to produce sugar nucleotide CMP-Leg5,7diN<sub>3</sub> and subsequent α2,6-sialyltransferase-catalyzed glycosylation, was achieved to synthesize the pentasaccharide.","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"49 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266912","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":"Regulating Molecular Structure of S,N-Heteroacene Non-fullerene Acceptors to Achieve Efficient Photoelectric Properties†","authors":"Mingtao Liu, Peipei Zhu, Shiting Lai, Xiage Zhang, Yuang Fu, Ling Xue, Dan Liu, Kui Feng, Xinhui Lu, Xugang Guo, Xunfan Liao, Yiwang Chen","doi":"10.1002/cjoc.202400699","DOIUrl":"https://doi.org/10.1002/cjoc.202400699","url":null,"abstract":"The ternary strategy has demonstrated its efficacy in improving charge transport in organic solar cells (OSCs). Here, three novel non-fullerene acceptors, SN6C9-4F, SN6C9-4Cl and SN6C10-4F, based on S,N-heteroacene linear backbone were designed and synthesized. The three acceptors exhibit excellent molecular coplanarity, high crystallinity and possess a deep-lying lowest unoccupied molecular orbital energy level, which is beneficial for charge transport and injection in organic field-effect transistors (OFETs). Notably, the OFET devices based on all three acceptors achieved impressive electron mobilities, with SN6C10-4F achieving up to 0.73 cm<sup>2</sup>·V<sup>–1</sup>·s<sup>–1</sup>, which is one of the highest values among A-D-A type small molecules. In addition, the OSCs device based on PBDB-T:SN6C9-4F exhibited the best power conversion efficiency of 12.07% owing to its optimal morphology and enhanced charge transport. Moreover, the incorporation of SN6C9-4F into the efficient PM6:L8-BO binary system to form ternary OSCs resulted in extended absorption range, enhanced donor crystallization, improved and more balanced charge transport, ultimately leading to an improvement of PCE from 17.78% to 18.32%. This study highlights the potential of developing acceptors with distinct structures from Y-series acceptors to broaden absorption and regulate donor crystallization, providing a novel approach to enhance the PCE of OSCs.","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"110 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142266909","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.202490202","DOIUrl":"https://doi.org/10.1002/cjoc.202490202","url":null,"abstract":"<p>The picture in the background is the old chemistry building of Soochow University, the symbols of S are: 1. for the research field of Prof. Wang Shunyi's group at Soochow University: Organic Sulfur Chemistry; 2. for Soochow University; 3. for Suzhou; 4. for Singapore. We would like to take this opportunity to celebrate the 110th anniversary of the founding of Chemistry and Chemical Engineering in Soochow University, as well as the 30th anniversary of the Suzhou-Singapore Industrial Park. The cover image portrays the reductive coupling reaction of xanthate esters with sulfur-containing and selenium-containing compounds (thio(seleno)sulfonates and disulfides(selenides)) under the nickel-catalyzed condition. It provides a mild and effective method for the synthesis of unsymmetric sulfides and selenides. More details are discussed in the article by Wang <i>et al</i>. on pages 2453—2458.\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 20","pages":"2422"},"PeriodicalIF":5.5,"publicationDate":"2024-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cjoc.202490202","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142234945","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}
Zhaoliang Yang, Chunlei Liu, Cheng Zhong, Jianye Zhang, Shengzhang Liu, mingming Yu, yangyang Li, Hong Yi, Aiwen Lei
{"title":"Electrochemical Carboarylation of Activated Alkenes with CO2 and Electron-deficient Aryl Bromides","authors":"Zhaoliang Yang, Chunlei Liu, Cheng Zhong, Jianye Zhang, Shengzhang Liu, mingming Yu, yangyang Li, Hong Yi, Aiwen Lei","doi":"10.1002/cjoc.202400661","DOIUrl":"10.1002/cjoc.202400661","url":null,"abstract":"<div>\u0000 \u0000 <p>The simultaneous construction of two vicinal C—C bonds in a molecule remains a significant challenge. In this work, we disclose an electroreductive carboarylation of activated alkenes under mild, transition metal-free conditions. Utilizing readily available starting materials (electron-deficient aryl bromides, activated alkenes, and CO<sub>2</sub>), this method demonstrates broad substrate scope and good functional group tolerance. Notably, this strategy enables the addition of two distinct electrophiles across an alkene in a highly chemo- and regioselective manner.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3367-3372"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195660","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}
Zhou Zhong, Xiang-Ji Liu, Li Ma, Zi-Jian Zhan, Yu-Xin Yuan, Heng-Jian Zhang, Feng-Ying Cai, Yi-Dong Hou, Jian Lü, Rong Cao
{"title":"Boosting Photogenerated Electrons Transfer from FeVO4 to Peroxymonosulfate via Cu Doping for Stable Degradation of Organic Contaminants","authors":"Zhou Zhong, Xiang-Ji Liu, Li Ma, Zi-Jian Zhan, Yu-Xin Yuan, Heng-Jian Zhang, Feng-Ying Cai, Yi-Dong Hou, Jian Lü, Rong Cao","doi":"10.1002/cjoc.202400669","DOIUrl":"10.1002/cjoc.202400669","url":null,"abstract":"<div>\u0000 \u0000 <p>Electron transfer is an important way to activate persulfate. Currently, the electrons for persulfate activation mainly originate from organic contaminants or the catalyst itself, which can lead to selective activation of persulfate or oxidation of the catalyst, respectively, and thus become a bottleneck restricting its application. In this work, Cu−doped FeVO<sub>4</sub> (Cu−FVO) was prepared, and the results showed that Cu doping can significantly improve the photocatalytic activity and stability of FVO for peroxymonosulfate (PMS) activation. The optimized Cu−FVO/PMS/light system exhibited a high BPA degradation rate that is 4.3 times higher than that of the FVO/PMS/light. This system manifested a broad applicability to various organic contaminants even with complex matrix. Photoelectrochemical analysis and DFT theoretical calculations revealed that Cu doping boosted the photogenerated charge separation and the adsorption of PMS on FVO. Furthermore, Cu doping led to the establishment of an electron transfer channel from Cu−FVO to PMS, through which photogenerated electrons achieved an efficient PMS activation. Meanwhile, holes were consumed by organic contaminants to avoid the oxidation of catalyst. These collectively enhanced the photocatalytic activity and stability of Cu−FVO, which also maintained high catalytic activity even after 20 cycling degradation reactions.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3201-3210"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195658","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}
Qin-Qin Song, Yue Guo, Peng Sun, Yao-Yue Fan, Kai-Long Ji
{"title":"Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii","authors":"Qin-Qin Song, Yue Guo, Peng Sun, Yao-Yue Fan, Kai-Long Ji","doi":"10.1002/cjoc.202400749","DOIUrl":"10.1002/cjoc.202400749","url":null,"abstract":"<div>\u0000 \u0000 <p>Five unreported and oxygenated <i>ent</i>-rosane diterpenoids (<i>ent</i>-RDs), Euphomillanols A—E (<b>1</b>—<b>5</b>), were isolated from <i>Euphorbia milii</i>. Among them, compounds <b>1</b> and <b>2</b> are unprecedented 7/7/6-fused tricyclic 5,10-seco-<i>ent</i>-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10),5-diene moiety, while <b>3</b> is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A. Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods, X-ray crystallography, and ECD calculation. Putative biosynthetic pathways for compounds <b>1</b>—<b>3</b> are proposed. All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes, and the most potent compound <b>4</b> showed an EC<sub>50</sub> value of 3.92 μmol/L with low cytotoxicity (IC<sub>50</sub> > 89.54 μmol/L).</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3211-3218"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195659","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}
Xiang Liu, Shaohong Ma, Shi Yan, Xiaotian Shi, Shuting Li, Yanlong Ma, Hua Cao
{"title":"Divergent Assembly of Functionalized Pyrazolo[1,5-a]pyridine Derivatives via [3+2] Cyclization of N-Aminopyridinium Salts with Various Unsaturated Hydrocarbons","authors":"Xiang Liu, Shaohong Ma, Shi Yan, Xiaotian Shi, Shuting Li, Yanlong Ma, Hua Cao","doi":"10.1002/cjoc.202400741","DOIUrl":"10.1002/cjoc.202400741","url":null,"abstract":"<div>\u0000 \u0000 <p>Two reaction modes for metal-free [3 + 2] cyclization of <i>N</i>-aminopyridinium derivatives with <i>β</i>-alkoxyvinyl trifluoromethylketones have been described through selective C—O or C—O/C—C bond cleavage. This strategy can also be extended to the [3 + 2] cyclization of <i>N</i>-aminopyridinium derivatives with enaminones and bromoalkynes. A broad range of <i>N</i>-aminopyridinium, <i>N</i>-aminoquinolinium, and <i>N</i>-aminoisoquinolinium salts are well tolerated, enabling the divergent synthesis of trifluoroacylated, non-substituted, acylated, and brominated pyrazolo[1,5-<i>a</i>]pyridine derivatives (62 examples).</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3355-3361"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195662","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":"To Maximize Luminescence for an Efficient Organic Solar Cell†","authors":"Yifei Geng, Tengfei Li, Zhenzhen Zhang, Yuze Lin","doi":"10.1002/cjoc.202400543","DOIUrl":"10.1002/cjoc.202400543","url":null,"abstract":"<div>\u0000 \u0000 <section>\u0000 \u0000 <h3> Comprehensive Summary</h3>\u0000 \u0000 <p>With the continuous development of photovoltaic materials, organic solar cells (OSCs) have made remarkable advancements, surpassing a power conversion efficiency (PCE) of 20%. However, the PCEs of OSCs remain lower than that of inorganic solar cells due to significant energy losses, mainly stemming from the relatively large non-radiative recombination losses (usually be expressed as ∆<i>E</i><sub>3</sub>), resulting in low open-circuit voltages. This can be achieved by reducing non-radiative recombination, and hereby increasing the electroluminescence quantum efficiency (EQE<sub>EL</sub>) of the photo-active layer. This review analyzes the significance of luminescence efficiency in achieving high-performance OSCs by examining the reciprocal relationship between ∆<i>E</i><sub>3</sub> and EQE<sub>EL</sub>. High-efficiency organic solar cells can also be used as effective organic light-emitting diodes (OLEDs). The discussion provides insights into the influencing factors of EQE<sub>EL</sub> and the mechanisms for adjusting various parameters, which include enhancements in photoluminescence quantum yield and the proportion of radiative excitons. The objective is to offer insights into the crucial role of luminescence performance in OSC development, guiding researchers toward developing novel photovoltaic materials or optimization strategies to enhance the luminescence performance of the active layer in OSCs, fostering the simultaneous advancement of OSCs and OLEDs.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p>\u0000 \u0000 </p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3157-3168"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195523","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":"Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ-Lactone","authors":"Xuerui Wang, Weiwu Ren","doi":"10.1002/cjoc.202400777","DOIUrl":"10.1002/cjoc.202400777","url":null,"abstract":"<div>\u0000 \u0000 <p>An efficient asymmetric [4+2] cyclization of hydroxyphenyl indolinone with azlactone for the synthesis of spirooxindole δ-lactone has been developed, which realized the first asymmetric reaction of hydroxyphenyl indolinone. A series of intricate structures with congested vicinal quaternary chiral centers were provided in good yields with excellent enantioselectivities via the <i>in situ</i> generated <i>o</i>-QM from hydroxyphenyl indolinone.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3362-3366"},"PeriodicalIF":5.5,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195653","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}