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Stereoselective synthesis of substituted 1,3-dienes from propargylic esters: electrophilic-metal or redox catalysis?

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Science China Chemistry 2024年第5期67卷 1384-1396页

作者： Mengfu Dai Liangliang Song Liang-An Chen Jiangsu Collaborative Innovation Center of Biomedical Functional Materials Jiangsu Key Laboratory of New Power BatteriesSchool of Chemistry and Materials ScienceNanjing Normal UniversityNanjing 210023China Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China

1,3-Diene architectures are not only widely present in natural products, pharmaceuticals, and functional organic materials but also serve as versatile building blocks to furnish important functionalized molecules in synthetic chemistry due to conjugated repeating C=C units. Accordingly, various strategies to access substituted 1,3-dienes in a stereoselective manner have been developed. However, chemo-, regio-and stereoselective synthesis of highly substituted 1,3-dienes still remains elusive and challenging. Readily available propargylic esters have emerged as an appealing class of synthetic intermediates for accessing functionalized 1,3-dienes, especially challenging tri-or tetrasubstituted variants, via transition-metal catalysis, including electrophilic metal and redox neutral catalysis. This review, for the first time, systematically highlights recent advances in transitionmetal catalyzed synthesis of substituted 1,3-dienes from propargylic esters, discusses the mechanisms and synthetic utilities, and gives the remaining challenges and potential opportunities in this field.

关键词： 1 3-diene propargylic ester Lewis acid redox catalysis transition metal

Simultaneous removal of 1,2-dichlorobenzene and furan over Mn-Ce-Fe oxide catalyst:Catalytic activity and product analysis

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Journal of Rare Earths 2024年第5期42卷 972-979,I0006页

作者： Juan Qiu Minghui Tang Yaqi Peng Xuanhao Guo Shengyong Lu Jianhua Yan Taizhou Institute of Zhejiang University Taizhou 318000China State Key Laboratory for Clean Energy Utilization Institute for Thermal Power EngineeringZhejiang UniversityHangzhou 310027China

The Mn-Ce-Fe mixed oxide(MCFe)was prepared by co-precipitation and the catalytic performance was tested by using 1,2-dichlorobenzene(1,2-DCB)and furan as model molecules of PCDD/*** effect of O_(2)concentration,SO_(2) and NO on the catalytic activity was *** 270℃,the MCFe oxide catalyst presents significant simultaneous removal efficiency of 75.25%and 100%for 1,2-DCB and furan,***-Emmett-Teller(BET)method(BET),X-ray diffraction(XRD),scanning electron microscopy(SEM),X-ray photoelectron spectroscopy(XPS),Fourier transform infrared spectroscopy(FTIR),H_2-temperature programmed reduction(H_(2)-TPR),NH_(3)-temperature programmed desorption(NH_3-TPD)and O_(2)-TPD were used to characterize the catalysts before and after the *** tests suggest that the oxidation behavior of furan occurred prior to that of 1,*** to the intermediate products detected by gas chromatography-mass spectrometry(GC-MS),the by-products include chlorinated hydrocarbons,long-chain hydrocarbons,ketone,*** catalytic oxidation reaction paths are proposed.

关键词： 1 2-dichlorobenzene Furan Catalytic oxidation Product analysis Rare earths

Nickel-catalyzed carbonylative four-component 1,4-dicarbofunctionalization of 1,3-enynes

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Science China Chemistry 2024年第6期67卷 2029-2038页

作者： Yan Zhao Qi-Chao Shan Hong Xin Pin Gao Xu Yang Xin-Hua Duan Li-Na Guo Department of Chemistry School of ChemistryXi’an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy StorageMaterials and DevicesMinistry of EducationXi’an Jiaotong UniversityXi’an710049China School of Electrical Engineering Xi’an Jiaotong UniversityXi’an710049China

An efficient Ni-catalyzed four-component 1,4-carbocarbonylation of 1,3-enynes with activated alkyl halides and arylboronic acids under atmospheric pressure of CO is *** tuning the electronic and steric effects of alkyl radicals,both electronrich and electron-deficient 1,3-enynes were compatible with this *** protocol features mild conditions,broad substrate scope,excellent functional group compatibility and facile gram-scale synthesis,providing a practical approach to the quaternary carbon center-containing allenyl *** study revealed that the acyl-NiIIspecies plays an important role in both the coupling and the alkyl radical generation processes.

关键词： Ni catalysis four-component 1 4-carbocarbonylation 1 3-enynes

Nickel-catalyzed arylcyanation of alkenes via cyano group translocation:access to 1,n-dinitriles or 4-amino nitriles

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Science China Chemistry 2024年第9期67卷 2975-2981页

作者： Xiaohong Li Shenfan Wang Xiangxiang Fu Donghui Xing Zeyuan Fu Yuanfu Deng Huanfeng Jiang Liangbin Huang State Key Laboratory of Pulp and Paper Engineering School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhou 510640China

Herein,a nickel-catalyzed arylcyanation of unactivated alkenes via cyano group translocation with aryl boronic acids has been *** transformations provided a robust approach to constructing structurally diverse 1,n-dinitriles or 4-amino nitriles from easily prepared and commercially available starting *** cyano group translocation was achieved,involving the addition into the intramolecular C–N triple bond followed by the retro-Thorpe *** studies revealed that high temperature and CsHCO_(3) as the base were crucial for the cyano group translocation.

关键词： arylcyanation nickel catalysis cyano group translocation 1 n-dinitriles 4-amino nitriles

Design,synthesis,and biological evaluation of 1,2,4-triazole derivatives as potent antitubercular agents

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Chinese Chemical Letters 2024年第3期35卷 326-331页

作者： Yu Wen Shichun Lun Yuxue Jiao Wei Zhang Tianyu Hu Ting Liu Fan Yang Jie Tang Bing Zhang William R.Bishai Li-Fang Yu Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China Center for Tuberculosis Research Department of MedicineDivision of Infectious DiseaseJohns Hopkins School of MedicineBaltimoreMD21231-1044United States Shanghai Institute for Advanced Immunochemical Studies and School of Life Science and Technology ShanghaiTech UniversityShanghai 201210China Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China

Inhibition of mycobacterial membrane protein large 3(MmpL3)thereby affecting the mycolic acid biosynthetic pathway has been proven to be an effective strategy for developing antitubercular *** on the X-ray crystal structure of MmpL3 inhibitor complexes,a series of novel 1,2,4-triazole derivatives were designed,synthesized and evaluated antitubercular activity against Mtb strain *** structure–activity relationship exploration resulted in the identification of compounds 21 and 28,which possess potent antitubercular activity against Mtb strain H37Rv[minimum inhibitory concentration(MIC)=0.03–0.13μg/mL]and the clinical isolates of multidrug resistance(MDR)and extensive drug resistance(XDR)tuberculosis(MIC=0.06–1.0μg/mL).Moreover,compounds 21 and 28 showed neglectable cytotoxicity(IC_(50)≥32μg/mL)to the mammalian Vero cells and favorable physicochemical and pharmacokinetic properties according to the in silico absorption,distribution,metabolism and excretion(ADME)***,the potential target of representative 1,2,4-triazole 28 was identified to be MmpL3 using a microscale thermophoresis(MST)assay.

关键词： Tuberculosis MDR and XDR-TB MmpL3 inhibitor 1 2 4-Triazole Structure-based drug design

Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates:A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives

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Chinese Chemical Letters 2024年第4期35卷 367-370页

作者： Zhiwei Chen Heyun Sheng Xue Li Menghan Chen Xin Li Qiuling Song Institute of Next Generation Matter Transformation College of Materials Science&Engineering and College of Chemical Engineering at Huaqiao UniversityXiamen 361021China Fujian University Key Laboratory of Molecule Synthesis and Function Discovery College of ChemistryFuzhou UniversityFuzhou 350108China State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

A practical method for the construction of difluoromethylene-containing 1,4-thiazine moieties using readily available diethyl bromodifluoromethanephosphonate(BrCF_(2)PO(OEt)_(2))as difluorocarbene precusor has been *** transformation features the efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates.A series of structurally novel and functionalized difluoromethylene-containing 1,4-thiazine derivatives were thus synthesized in good yields.

关键词： Difluoromethylene Pyridinium 1 4-zwitterionic thiolates 1 4-Thiazine derivatives

Synthesis of Unprotectedα-Tertiary Amines and 1,2-Amino Alcohols from Vinyl Azides by Light Induced Denitrogenative Alkylarylation/Dialkylation

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CCS Chemistry 2024年第4期6卷 1060-1070页

作者： Sifan Li Hai-Wu Du Paul W.Davies Wei Shu Department of Chemistry Shenzhen Grubbs InstituteSouthern University of Science and TechnologyShenzhen 518055Guangdong School of Chemistry University of BirminghamEdgbastonBirmingham B152TT

Sterically congestedα-tertiary primary amines are ubiquitous substructures in pharmaceutical and agrochemical agents yet are challenging to ***,straightforward photoredox-catalyzed access to structurally diverseα,α,α-trisubstituted primary amines from denitrogenative alkylarylation or dialkylation of vinyl azides with N-hydroxyphthalimide(NHPI)esters and cyanoarenes or aryl aldehydes has been *** use of vinyl azide as a precursor to a primary aminewas enabled by the dual role of the Hantzsch ester to form an electron donor-acceptor complex and serve as a sacrificial *** strategy provides a modular synthesis ofα-tertiary primary amines,including unprotected 1,2-amino alcohols,from simple materials with excellent functional group *** synthetic applicability of this method was demonstrated by streamlined access to 2,2-disubstituted *** investigations support two parallel reductive photocatalytic cycles allowing for the denitrogenative alkylarylation or dialkylation of vinyl azides via decarboxylative radical addition followed by heteroradical cross-coupling betweenα-amino radicals and aryl anion radicals or ketyl anion radicals.

关键词： photocatalysis α-tertiary primary amines 1 2-amino alcohols vinyl azide electron donor-acceptor complex

铁氮共改性MCM-41活化过硫酸盐去除地下水中1,2-二氯乙烷

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环境科学学报 2024年第1期44卷 265-274页

作者：孟宪荣闫兴雨魏晨军施维林许伟苏州市环境科学研究所江苏省博士后创新实践基地苏州215009 苏州科技大学环境科学与工程学院苏州215009

采用一步水热法将氨基(—NH_(2))和铁(Fe)共同引入到介孔材料MCM-41中,合成改性介孔材料Fe-NH_(2)-MCM-41,构建Fe-NH_(2)-MCM-41/过二硫酸盐(persulfate,PDS)体系去除水中1,2-二氯乙烷(1,2-DCA).利用扫描电子显微镜(SEM)、X射线衍射(XRD)、BET比表面积测试法和傅里叶红外(FTIR)对材料进行表征,考察了PDS投加节点、pH、阴离子和腐殖酸对Fe-NH_(2)-MCM-41/PDS体系去除1,2-DCA的影响,并利用电子自旋共振(EPR)和自由基猝灭实验确定反应活性物种,揭示反应机理.结果显示:—NH_(2)和Fe的引入均使材料具有了PDS活化能力,而—NH_(2)和Fe同时引入则进一步强化了材料的活化性能,使1,2-DCA去除率提高了37.3%.Fe-NH_(2)-MCM-41/PDS体系对pH具有较宽的适用范围,在pH为3~9范围内对1,2-DCA去除率稳定在55%左右.该体系还具有良好的抗离子干扰能力,地下水常见阴离子在较低和较高浓度条件下均对Fe-NH_(2)-MCM-41/PDS体系去除1,2-DCA影响较小,Cl-具有轻微促进作用,NO_(3)-、SO_(4)^(2−)呈轻微抑制作用;腐殖酸(HA)浓度较高时才抑制1,2-DCA的降解,地下水中HA(浓度一般为0.1~10 mg·L^(-1))不足以对Fe-NH_(2)-MCM-41/PDS体系降解1,2-DCA起到明显的抑制作用.自由基及EPR测试证明Fe-NH_(2)-MCM-41/PDS体系降解1,2-DCA主要机制为自由基反应机制,主要活性物种为S0_(4)^(·-)、·OH和O_(2)^(·-).

关键词： MCM-41 铁氮共改性高级氧化技术过硫酸盐 1 2-二氯乙烷

铑催化7-辛烯醛氢甲酰化反应合成1,9-壬二醛

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分子催化（中英文） 2024年第2期38卷 160-170,I0005页

作者：刘传卓李志坚汤易天李永刚董开武上海中化科技有限公司上海201315 华东师范大学化学与分子工程学院上海200062

脂肪族二醛是一类重要的工业化学品中间体,可以经过氧化、还原、还原酯化、还原胺化等反应获得二酸、二醇、二酯、二胺等各种重要的化学品.我们报道了一种以丁二烯下游中间体—7-辛烯醛为原料的铑催化氢甲酰化反应合成1,9-壬二醛的方法... 详细信息

脂肪族二醛是一类重要的工业化学品中间体,可以经过氧化、还原、还原酯化、还原胺化等反应获得二酸、二醇、二酯、二胺等各种重要的化学品.我们报道了一种以丁二烯下游中间体—7-辛烯醛为原料的铑催化氢甲酰化反应合成1,9-壬二醛的方法,考察了不同膦配体对催化剂性能的影响,对反应工艺条件进行了研究和优化.使用Rh(I)/Xantphos催化剂,较优工艺条件下, 7-辛烯醛转化率>99%,直链壬二醛收率86%,醛产物正异比27, TON可达49 500.最后,对7-辛烯醛的氢甲酰化主反应和副反应机理进行了探讨.

关键词： 1 9-壬二醛 7-辛烯醛氢甲酰化 Xantphos 铑