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Highly active organocatalyst from a trivalent phosphazenium salt for ring-opening copolymerization of epoxides and cyclic anhydrides enhanced by hydrogen bonding interactions

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Science China Chemistry 2024年第9期67卷 3111-3120页

作者： Chunhuan Jiang Junqi Wang Xiaoyu Liu Xiaoxia You Ronglin Zhong Chuanli Ren Zhibo Li Key Laboratory of Biobased Polymer Materials Shandong Provincial Education DepartmentCollege of Polymer Science and EngineeringQingdao University of Science and TechnologyQingdao 266042China College of Chemical Engineering Qingdao University of Science and TechnologyQingdao 266042China Laboratory of Theoretical and Computational Chemistry Institute of Theoretical ChemistryCollege of ChemistryJilin UniversityChangchun 130012China

It is highly desirable to develop simple organocatalysts for the controlled ring-opening alternating copolymerization(ROAC)of epoxides and cyclic anhydrides,leading to high molecular weight ***,a phosphazenium salt,namely tri[tris(dimethylamino)phosphoranylidenamino]phosphonium chloride(P_(4)^(+)Cl^(-)),is developed as a catalyst for the ROAC of epoxides and cyclic ***,the combination of P_(4)^(+)Cl^(-)with a protonic initiator,such as 1,4-benzenedimethanol(BDM)exhibited high efficiency in the copolymerization of propylene oxide(PO)and phthalic anhydride(PA).This led to the production of polyester with an exceptional high molecular weight(M_n)of up to 126 k Da,which represented a rare example of poly(PO-alt-PA)with Mnsurpassing 100 k *** that the core P atom is trivalent status and the tris[tris(dimethylamino)]phosphoranyl group will share one proton in the P_(4)^(+)Cl^(-)*** combined with protonic species,the P_(4)^(+)Cl^(-)will not only serve as a proton acceptor but also as a hydrogen bonding donor for the cyclic ***,it was assumed that the P_(4)^(+)plus proton served dual role in mimic of base/urea pair to effectively catalyze ROAC,which was supported by density functional theory(DFT)calculations.

关键词： ring-opening copolymerization organocatalyst epoxides cyclic anhydrides phosphazenium salt

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Silica Chloride Nano Particle Catalyzed Ring Opening of epoxides by Aromatic Amines

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Chinese Journal of Chemistry 2011年第5期29卷 955-958页

作者： Karimian Ramin Piri Farideh Karimi Babak Moghimi Abolghasem Department of Chemistry Faculty of Science Zanjan University P.O. Box 45195-313 Zanjan LR. Iran Department of Chemistry Institute for Advanced Studies in Basic Sciences (1ASBS) P.O. Box 45195-1159 Gava Zang Zanjan Iran Department of Chemistry Imam Hossein University P.O. Box 16575-347 Tehran Iran

Silica chloride nano particle （nano SiO2-C1）, has been found to be heterogeneous catalyst for facile, simple and mild ring opening of epoxides with aromatic amines to afford β-amino alcohols in dry CH2C12 at room t... 详细信息

关键词： silica chloride nano particle epoxides catalyzed ring opening

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Remarkably Accelerated Regioselective Hydrogenolysis of Terminal epoxides in the Presence of CoCl_2 or NiSO_4

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Chinese Journal of Chemistry 2003年第7期21卷 972-974页

作者：沈鑫唐朝军伍贻康 State Key Laboratory of Bioorganic & Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

The rate of atmospheric pressure hydrogenolysis of terminal e-poxides over palladium-charcoal to the corresponding methyl alcohols could be remarkably accelerated by introduction of Co-Cl2 or NiSO4.

关键词： epoxides hydrogenolysis cobalt nickel ring-open-ing

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CYP1B1-derived epoxides modulate the TRPA1channel in chronic pain

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Acta Pharmaceutica Sinica B 2023年第1期13卷 68-81页

作者： Lili Sun Jie Zhang Changshan Niu Cassandra E.Deering-Rice Ronald W.Hughen John G.Lamb Katherine Rose Kevin M.Chase Marysol Almestica-Roberts Markel Walter Eric W.Schmidt Alan R.Light Baldomero M.Olivera Christopher A.Reilly Department of Pharmacology and Toxicology Center for Human ToxicologyUniversity of UtahSalt Lake CityUT84112USA Department of Anesthesiology School of MedicineUniversity of UtahSalt Lake CityUT 84112USA Department of Medicinal Chemistry University of UtahSalt Lake CityUT 84112USA School of Biological Sciences University of UtahSalt Lake CityUT 84112USA

Pain is often debilitating,and current treatments are neither universally efficacious nor without *** receptor potential(TRP)ion channels offer alternative targets for pain relief,but little is known about the regulation or identities of endogenous TRP ligands that affect inflammation and ***,transcriptomic and targeted lipidomic analysis of damaged tissue from the mouse spinal nerve ligation(SNL)-induced chronic pain model revealed a time-dependent increase in Cyp1b1 mRNA and a concurrent accumulation of 8,9-epoxyeicosatrienoic acid(EET)and 19,20-EpDPA post *** of 8,9-EET and 19,20-EpDPA by human/mouse CYP1B1 was confirmed in vitro,and 8,9-EET and 19,20-EpDPA selectively and dose-dependently sensitized and activated TRPA1 in overexpressing HEK-293 cells and Trpa1-expressing/AITC-responsive cultured mouse peptidergic dorsal root ganglia(DRG)***1 activation by 8,9-EET and 19,20-EpDPA was attenuated by the antagonist A967079,and mouse TRPA1 was more responsive to 8,9-EET and 19,20-EpDPA than human *** latter effect mapped to residues Y933,G939,and S921 of ***-plantar injection of 19,20-EpDPA induced acute mechanical,but not thermal hypersensitivity in mice,which was also blocked by ***,Cyp1b1-knockout mice displayed a reduced chronic pain phenotype following SNL *** data suggest that manipulation of the CYP1B1-oxylipin-TRPA1 axis might have therapeutic benefit.

关键词： CYPIB1 Spinal nerve ligation epoxides TRPA1 Calcium imaging Hyperalgesia Chronic pain Inflammation

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Chiral metal-containing ionic liquid:Synthesis and applications in the enantioselective cycloaddition of carbon dioxide to epoxides

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Science China Chemistry 2011年第7期54卷 1044-1050页

作者： SONG YingYing JIN QianRu ZHANG SuLing JING HuanWang ZHU QianQian State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical EngineeringLanzhou UniversityLanzhou 730000China

A series of novel chiral metal-containing ionic liquids (CMILs) consisting of the cation of crown ether-chelated potassium/ sodium and the anion of chiral amino acids were designed and synthesized. These new CMILs were used to catalyze the enantioselective cycloaddition of epoxides and carbon dioxide incorporating with the salenCo(OOCCC13) to generate corresponding chiral cyclic carbonates under mild conditions. These new catalysts can be recycled at least five times without significant loss of activity and enantioselectivity.

关键词： chiral metal-containing ionic liquids epoxides carbon dioxide enantioselective cycioaddition chiral cyclic carbonates

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Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO_(2)

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Chinese Chemical Letters 2024年第7期35卷 281-284页

作者： Tian-Yu Gao Xiao-Yan Mo Shu-Rong Zhang Yuan-Xu Jiang Shu-Ping Luo Jian-Heng Ye Da-Gang Yu Key Laboratory of Green Chemistry&Technology of Ministry of Education College of ChemistrySichuan UniversityChengdu 610064China State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology Zhejiang University of TechnologyHangzhou 310014China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

Herein, we report the first visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO_(2)to synthesize hydroxy acid derivatives. A variety of valuable β-, γ-, δ-, ε–hydroxy acid derivatives are obtained in moderate to high yields under mild conditions. This protocol shows noteworthy functionalgroup compatibility, high chemo-and regioselectivities under transition-metal-free conditions with an inexpensive organo-dye as photosensitizer. Mechanistic studies indicate that the benzylic carbanion is generated as an intermediate via the sequential single electron transfer(SSET) process.

关键词： Carbon dioxide epoxides Visible-light photoredox catalysis Hydroxy acid Sequential single electron transfer

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Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides

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Science China Chemistry 2010年第6期53卷 1294-1301页

作者： CHEN GuoHong,WANG Xin,JIN XiaoQian,LIU LingYan,CHANG WeiXing & LI Jing State Key Laboratory and Research Institute of Elemento-organic Chemistry,Nankai University,Tianjin 300071,China 1. State Key Laboratory and Research Institute of Elemento-organic Chemistry Nankai University Tianjin 300071 China

This paper presents a versatile reagent for epoxide *** allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions,*** could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.

关键词： versatile reagent allyltin tribromide ring opening of epoxides room temperature

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H_(3)PMo_(12)O_(40)-catalyzed coupling of diarylmethanols with epoxides/diols/aldehydes toward polyaryl-substituted aldehydes

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Chinese Chemical Letters 2020年第12期31卷 3233-3236页

作者： Guoping Yang Yufeng Liu Ke Li Wei Liu Bing Yu Changwen Hu Key laboratory of Cluster Science of Ministry of Education.Beijing Key Laboratory of Photoelectronic/Elecrophotonic School of chemistry and Chemicad EngineeringBeijing Instirute of TechnologyBeijing 100081China Jiangxi Key Laboratory for Mass Spectrormetry and Instrunentation East China University of TechnologyNanchang 330013China Green Catalysis Center College of ChemistryZhengzhou UniversityZhengzhou 450001China

A versatile heteropoly acid(H_(3)PMo_(12)O_(40))-catalyzed coupling of diarylmethanols with epoxides was established for the synthesis of polyaryl-substituted ***,the catalytic system was also suitable for the reaction of diarylmethanols and diols/*** application of such an earthabundant,readily accessible,and nontoxic catalyst provides a green approach for the construction of polyaryl-substituted aldehydes.

关键词： Polyoxometalates Diarylmethanols epoxides Polysubstituted aldehydes Acid catalysis

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H_(4)SiW_(12)O_(40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3,4-disubstituted 1H-pyrazoles

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Chinese Chemical Letters 2022年第3期33卷 1483-1487页

作者： Guoping Yang Xuanjie Xie Mengyuan Cheng Xiaofei Gao Xiaoling Lin Ke Li Yuanyuan Cheng Yufeng Liu Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation Jiangxi Province Key Laboratory of Synthetic ChemistryEast China University of TechnologyNanchang 330013China Henan Key Laboratory of Polyoxometalate Chemistry College of Chemistry and Chemical EngineeringHenan UniversityKaifeng 475004China

A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H_(4)SiW_(12)O_(40))-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3,4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3,4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.

关键词： Silicotungstic acid epoxides Aldehydes Sulfonyl hydrazides 3,4-Disubstituted 1H-pyrazoles

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Advances in Electrochemical Oxidation of Olefins to epoxides

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CCS Chemistry 2023年第5期5卷 1028-1042页

作者： Peng Zhang Tuo Wang Jinlong Gong Key Laboratory for Green Chemical Technology of Ministry of Education School of Chemical Engineering and TechnologyTianjin UniversityTianjin 300072 Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Tianjin 300072 National Industry-Education Platform of Energy Storage Tianjin UniversityTianjin 300350 Haihe Laboratory of Sustainable Chemical Transformations Tianjin 300192 Joint School of National University of Singapore and Tianjin University International Campus of Tianjin UniversityBinhai New CityFuzhou 350207Fujian

epoxides are important chemicals and used in multiple *** conventional thermal-catalytic production of epoxides consumes a large amount of energy and generates abundant carbon ***,sustainable manufacturing technologies are highly *** advantage of renewable electricity to drive electrochemical epoxidation reactions provides a novel approach to generating value-added products in the chemicals *** review describes the current progress of selective electrochemical oxidation of olefins to epoxides,which is categorized according to the different reaction *** halide-mediated method is first discussed,followed by an overview of electrochemical epoxidations with H_(2)O and O_(2)-derived H_(2)O_(2).Moreover,the existing problems in this fast-growing field and future developing directions are pointed *** review hopes to provide inspiration for the design of electrocatalysts,electrode materials,and electrolyzers for the electrochemical production of epoxides in a sustainable manner.

关键词： electrochemistry selective oxidation olefins epoxides power-to-X

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