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Palladium-Catalyzed Cascade Double C--N Bond Activation： A New Strategy for Aminomethylation of 1,3-Dienes with Aminals

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Chinese Journal of Chemistry 2018年第10期36卷 929-933页

作者： Cuifang Qiao Anrong Chen Bingjian Gao Yang Liu Hanmin Huang Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry Center for Excellence in Molecular Synthesis University of Science and Technology of China Chinese Academy of Sci- ences Hefei Anhui 230026 China State Key Laboratory for Oxo Synthesis and Setective Oxidation Lanzhou institute of Chemical Physics Chinese Academy of Sciences Lanzhou Gansu 730000 China

A new palladium-catalyzed selective aminomethylation of conjugated 1,3-dienes with aminais via double C-N bond activation is described. This simple method provides an effective and rapid approach for the synthesis of linear a,13-unsaturated allylic amines with perfect regioselectivity. Mechanistic studies disclosed that one palladium catalyst cleaved two distinct C-N bond to furnish a cascade double C-N bond activation, in which an allylic 1,3-diamine and allylic 1,2-diamine were initially formed as key intermediates through the palladium-catalyzed C-N bond activation of aminal and the α,β-unsaturated allylic amine was subsequently produced via palladium-catalyzed C-N bond activation of the allylic diamines.

关键词： aminomethylation 1,3-diene amine C-N bond activation allyic compounds synthetic methods

Machine learning-assisted systematical polymerization planning:case studies on reversible-deactivation radical polymerization

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Science China Chemistry 2021年第6期64卷 1039-1046页

作者： Yu Gu Peirong Lin Chengda Zhou Mao Chen State Key Laboratory of Molecular Engineering of Polymers Department of Macromolecular ScienceFudan UniversityShanghai 200433China Department of Civil and Environmental Engineering Princeton UniversityNew Jersey 08544USA

The combined influence of chemical composition,molecular weight(MW)and molecular weight distribution(D)on the functions and performances of polymeric materials necessitates simultaneous satisfaction of multidimensional requirements during polymer synthesis.However,the complexity of polymerization reactions often dissuades chemists when precisely accessing diversified polymer targets.Herein,we developed a machine learning(ML)-assisted systematical polymerization planning(SPP)platform for addressing this challenge.With ML model providing integrated navigation of the reaction space,this approach can conduct multivariate analysis to uncover complex interactions between the polymerization result and conditions,prescribing optimal reaction conditions to achieve discretionary polymer targets concerning three dimensions including chemical composition,MWandD values.Given the increasing importance of polymerization in advanced material engineering,this ML-assisted SPP platform provides a universal strategy to access tailored polymers with on-demand prediction of polymerization parameters.

关键词： polymerization synthetic methods synthesis planning photochemistry machine learning

Facile Generation of Strained Peptidyl Thiolactones from Hydrazides and Its Application in Assembling MUC-1 VNTR OIigomers

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Chinese Journal of Chemistry 2021年第9期39卷 2509-2516页

作者： Yuankun Dao Biao Wang Weidong Dong Jun Zhang Chao Zhong Zhili Zhang Suwei Dong State Key Laboratory of Natural and Biomimetic Drugs and Department of Chemical BiologySchool of Pharmaceutical SciencesPeking UniversityBeijing 100191China Institute of Systems Biomedicine School of Basic Medical SciencesPeking University Health Science CenterBeijing 100191China

An efficient method for the activation of C-terminal 4-mecaptoproline-or penicillamine-containing peptide hydrazides in ligation re-actions is reported herein.The corresp on ding peptide hydrazides can be readily prepared using solid-phase peptide synthesis,and subsequently activated by acetylacet one(acac)without exoge nous thiol additives.Strained peptidyl thiolactones could be the possible reactive in termediates that drastically accelerate the reacti on rates at the sterically demandi ng proline and valine sites.This developed protocol allows for sequential peptide ligations in a one-pot manner,and expedites the assembly of mucin 1(MUC-1)variable number tandem repeat(VNTR)trimers in various glycosylated forms.

关键词： Strained molecules Glycopeptides synthetic methods Peptidyl thiolactones

Base-mediated formal [3＋2] cycloaddition of β,γ-alkenyl esters and p-TsN3 for the synthesis of pyrazoles

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Science Bulletin 2017年第7期62卷 493-496页

作者： Mi-Na Zhao Mei-Na Zhang Zhi-Hui Ren Yao-Yu Wang Zheng-Hui Guan Key Laboratory of synthetic and Natural Functional Molecule Chemistry of Ministry of Education Department of Chemistry & Materials ScienceNorthwest University

A novel 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU)-mediated formal cycloaddition of β,γ-alkenyl esters with p-tolylsulfonylazide(p-TsN_3) for the synthesis of 3,5-disubstituted pyrazoles has been developed.The reaction proceeded through diazotization of β,γ-alkenyl esters sequential with thermodynamic cyclization.p-Tolylsulfonylazide played a role as a source of two-nitrogen synthons.The reaction employs readily available starting materials,tolerates a wide range of functional groups,and proceeds under mild conditions.

关键词： synthetic methods Cycloaddition β,γ-Alkenylesters p-Tolylsulfonylazide Pyrazoles

Direct synthesis of benzoxazinones via Cp*Co(Ⅲ)-catalyzed C-H activation and annulation of sulfoxonium ylides with dioxazolones

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Chinese Chemical Letters 2021年第3期32卷 1263-1266页

作者： Yongqi Yu Zhen Xia Qianlong Wu Da Liu Lin Yu Yuanjiu Xiao Ze Tan Wei Deng Gangguo Zhu State Key Laboratory of Chemo/Biosensing and Chemometrics College of Chemistry and Chemical EngineeringHunan UniversityChangsha 410082China Department of Chemistry Zhejiang Normal UniversityJinhua 321004China

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(Ⅲ)-catalyzed C-H activation and[3+3]annulation between sulfoxonium ylides and dioxazolones.The reaction is conducted under base-free conditions and tolerates various functional groups.Starting from diverse readily available sulfoxonium ylides and dioxazolones,a variety of benzoxazinones could be synthesized in one step in 32%-75%yields.

关键词： C-H activation Cobalt catalysis Annulations Sulfoxonium ylides synthetic methods

Use of a Removable Backbone Modification Strategy to Prevent Aspartimide Formation in the Synthesis of Asp Lactam Cyclic Peptides

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Chinese Journal of Chemistry 2021年第9期39卷 2517-2522页

作者： Tingting Cui Junyou Chen Rui Zhao Yanyan Guo JiahuiTang Yulei Li Yi-Ming Li Donald Bierer Lei Liu School of Food and Biological Engineering Engineering Research Center of Bio-processMinistry of EducationHefei University of TechnologyHefeiAnhui 230009China Tsinghua-Peking Center for Life Sciences Ministry of Education Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical BiologyCenter for Synthetic and Systems BiologyDepartment of ChemistryTsinghua UniversityBeijing 100084China Department of Medicinal Chemistry Bayer AGAprather Weg 18A42096 WuppertalGermany Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026China

The synthesis of an Asp lactam derivative of A-183,a selective inhibitor of Factor 7a with good anticoagulant and antithrombotic activity,is described.Our synthesis depends on the use of a removable backbone modification(RBM)strategy to prevent aspartimide formation,which thwarted all attempts to synthesize this target using direct solid-phase peptide synthesis.Validation of the RBM strategy in the synthesis of a second Asp lactam derivative was also accomplished.The RBM strategy is therefore proposed as a general method for the synthesis of Asp lactam cyclic peptides.

关键词： Peptides Solid-phase synthesis synthetic methods Aspartimide Lactam cyclic peptides

Synthesis of 2（5H）-Furanone Derivatives with Bis-1,2,3-triazole Structure

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Chinese Journal of Chemistry 2012年第10期30卷 2411-2422页

作者：霍景沛吕梅香汪朝阳李意忠 School of Chemistry and Environment South China Normal UniversityGuangzhouGuangdong 510006China

A series of new chiral 2（5H）-furanone derivatives containing bis-l,2,3-triazole moiety were designed and syn- thesized from （5S）-5-alkoxy-3,4-dihalo-2（5H）-furanones 1, dicarboxyl amino acids 2, propargyl bromide, and or- ganic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addi- tion-elimination, substitution and no-ligand click reaction. Twelve new intermediates, including N-[5-alkoxy- 2（5H）-furanonyl] dicarboxyl amino acids 3 and their corresponding propargyl esters 4, and twelve target molecules 6 were characterized by FTIR, 1H NMR, 13C NMR, MS and elemental analysis. The influences of different syn- thetic conditions and substrates in each step were investigated. The research provides a new method and idea for the synthesis of 2（5H）-furanone compounds with polyheterocyclic structure due to the diversities of four basic unit molecules.

关键词： 2（5/4）-furanone bis-1,2,3-triazole amino acids synthetic methods click chemistry

Cu/Picolinamides-Catalyzed Coupling of (Hetero) aryl Halides with Secondary Phosphine Oxides and Phosphite

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Chinese Journal of Chemistry 2021年第11期39卷 2957-2961页

作者： Chao Fang Bangguo Wei Dawei Ma Department of Natural Medicine School of PharmacyFudan University826 Zhangheng RoadShanghai201203 China State Key Laboratory of Bioorganic&Natural Products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai200032 China

Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of(hetero)aryl halides with secondary phosphine oxides and phosphites.Only 3—5 mol%CuI and ligands were r... 详细信息

关键词： synthetic methods Cross-Coupling Aryl halides Copper Aryl phosphine oxides

Base-Promoted Formylation and N-Difluoromethylation of Azaindoles with Ethyl Bromodifluoroacetate as a Carbon Source

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Chinese Journal of Chemistry 2021年第6期39卷 1477-1482页

作者： Yang Li Ning Sun Cai-Lin Zhang Meng Hao Xi'an Key Laboratory of Textile Chemical Engineering Auxiliaries School of Environmental and Chemical EngineeringXi'an Polytechnic UniversityXi'anShaanxi 710048China

We reported for the first time that ethyl bromodifluoroacetate directly reacts with azaindole without transition metal catalysis to produce a difluoromethyl protected 5-aldehyde group product in one step.It is worth mentioning that the reacted aldehyde group is only formed at the 5 position.In addition,this method has good substrate applicability and functional group tolerance.Finally,we also carried out some mechanism auxiliary experiments,which confirmed that the aldehyde-based carbon comes from ethyl bromodifluoroacetate.

关键词： Azaindoles C1 building blocks Difluoromethylene Hydrolysis synthetic methods