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    Home > Professor Wu Lei, Nanjing Agricultural University Research Group: binanyl nano palladium catalyzed Alkynylation and highly selective hydrogenation in series to construct phosphoryl (z) - [3] dendrarenes

    Professor Wu Lei, Nanjing Agricultural University Research Group: binanyl nano palladium catalyzed Alkynylation and highly selective hydrogenation in series to construct phosphoryl (z) - [3] dendrarenes

    • Last Update: 2019-10-20
    • Source: Internet
    • Author: User
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    In recent years, as a kind of acyclic cross conjugated oligoolefins, dendralenes has attracted more and more attention due to its unique structure and application value

    Although (z) - [3] dendralenes are widely found in natural products such as plant essential oil and bilirubin, its stereoselective synthesis is still the most challenging field, especially the synthesis method of (Z, z) - [3] dendralenes has only two reports at present, but its stereoselectivity is poor or its yield is low

    Advanced synthesis & catalyst, 2016, 358, 3039; catalyst Science & technology, 2017, 7, 5515) and phosphoryl [3] dendralenes (ACS catalyst sis, 2017, 7, Based on the research of (181), the series Alkynylation and highly selective hydrogenation of (z) and (Z, z) - [3] dendralenes with binaryl palladium nanocatalyst were successfully developed

    In addition, this paper has carried out a variety of derivative studies on (z) - [3] dendralenes

    Related work was published in org


    (DOI: 10.1021 / ACS



    Brief introduction of Professor Wu Lei's research group in recent years, Professor Wu Lei's research group has focused on the synthesis methods of functional organophosphorus compounds and heterocyclic compounds and nano catalytic materials, etc., in ACS catalyst, org

    Lett., chem

    Commun., org


    Front., adv


    Catalyst., catalyst


    Technol., J


    Chem, Chem



    and other international journal systems published many achievements


    Wu Lei, born in 1980, professor and doctoral supervisor of Nanjing Agricultural University, vice president of School of science

    In 2007, he graduated from the Institute of chemistry, Chinese Academy of Sciences, under the guidance of researcher fan Qinghua

    From 2007 to 2010, he was engaged in postdoctoral research in Syracuse University and University of Notre Dame in the United States

    From 2010 to 2012, he worked in the Institute of basic and interdisciplinary sciences of Harbin University of Technology (introduced by Harbin University of technology's "hundred talents plan"), and entered Nanjing Agricultural University in August 2012

    It has been selected as the "blue and blue project" of Jiangsu Province, the "333 high-level talent training project" of Jiangsu Province and the "excellent graduate teacher" of Nanjing Agricultural University

    The main research fields are heteroatom chemistry and metal nano catalysis materials

    He has successively presided over many scientific research projects, such as the National Natural Science Foundation of China, Jiangsu Natural Science Foundation, the research start-up project of returned overseas students of the Ministry of education, the start-up fund of high-level talents introduction of Nanjing Agricultural University, and the start-up fund of talents introduction of Harbin University of industry

    He has been in ACS catalyst, org

    Lett., chem Commin., J


    Chem., chem


    J., adv


    Catalyst., catalyst



    And other international authoritative journals published more than 40 SCI papers by corresponding authors, with H index of 20, he cited more than 1000 times, and 3 research papers were selected into "ESI high cited papers"

    He is the reviewer of SCI journals at home and abroad, such as organic chemistry, Journal of chemistry, ACS catalyst, green chem., org

    Lett., adv


    Catalyst., chem



    Leading scientific research achievements: binanyl nano palladium catalyzes Alkynylation and highly selective hydrogenation in series to build phosphoryl (z) - [3] dentralenes as shown in Figure 1

    The author first attempts to optimize the reaction under the condition of hydrogen balloon, using 2 mol% bin pdnps (binanyl nano palladium) as catalyst, taking phosphine to replace diene (1a) and phenylacetylene as substrates

    As shown in Figure 2, solvents and bases play an important role in the reaction

    The optimum conditions were found in DMF and the target product 2a was obtained in 83% yield

    At the same time, the products 2A 'and 2A "of further hydrogenation were observed in the process of condition exploration

    It is worth mentioning that both heterogeneous Lindlar and Pd / C catalysts have no catalytic activity for the series reaction

    Although PD (PPh3) 4 and Pd (PPh3) 2Cl2 obtained a certain amount of 2a, their catalytic efficiency and regioselectivity could not be controlled


    1 bin pdnps catalyses the series reaction of Phos substituted diene with phenylacetylene (source: org

    Lett.) Fig

    2 condition screening (source: org

    Lett.) after determining the optimal reaction conditions, the author first studied the applicability of alkyne substrate (Fig


    Generally, for arylalkynes, the electron donating effect is observed

    When the para substituent of arylalkyne has electron donating group (such as methyl, ethyl, tert butyl, phenyl and methoxy), the reaction can get quite good yield (2b-f), especially, when the para is methoxy, the reaction can get 91% yield

    When there are electron absorbing substituents on the aryl group, including P-F, p-cn and p-no2, it is not conducive to the occurrence of the reaction, and only the medium yield can be obtained

    When the p-position is phenyl, the yield may be reduced due to the steric hindrance

    At the same time, when the para group is ester group, 80% yield can also be obtained

    The mild and high selectivity of the reaction can also be explained by the substrate with nitro group, which can be maintained in the final product (2J)

    It is worth mentioning that this method can also be applied to heteroaromatic alkynes, and 3-pyridyl and 2-thiophenyl alkynes can also be obtained in medium to good yields (2m and 2n), so as to obtain a new kind of heterocyclic substituted dendrarenes

    Aliphatic alkynes, such as isopropenylacetylene and 1-octyne, can also react

    It is worth noting that in the case of isopropenylacetylene, the distal non conjugate double bond is also hydrogenated to obtain compound 2O in 72% yield


    3 substrate universality study (source: org

    Lett.) next, the author studied the reaction of acyclic compounds at the end of diene

    The results showed that the corresponding products could be obtained with better yield and chemical selectivity

    It is worth mentioning that the change of R 1 and R 2 groups will generate Z, Z - [3] dendralenes

    When unsymmetrical p-o-substituted dienes are used to react with aromatic alkynes without substituents, the target products of Z, Z configuration can be obtained with high chemical selectivity

    When the arylalkynes contain electron acceptors, such as fluorine substitution, the selectivity is significantly reduced

    However, when the arylalkynes contain electron acceptors, such as p-methoxyphenyl and β - naphthyl alkyne substrates, the proportion of Z and Z configuration of the corresponding products is increased

    The stereoselectivity of phos-o-substituted diene is very poor when the terminal of phos-o-substituted diene contains asymmetric chain alkyl


    4 substrate universality study (source: org

    Lett.) in order to further prove the potential application value of the reaction, the author conducted gram scale-up of the reaction and carried out a variety of derivative studies of (z) - [3] dendralenes (Fig



    5 gram level reaction and product derivatization (source: org

    Lett.) to sum up, based on the high-efficiency catalytic ability of binanyl palladium nano catalyst (bin pdnps), the author developed a new high-efficiency selective synthesis strategy of phosphoryl-z and Z, Z - [3] dendralenes

    The Alkynylation and highly selective hydrogenation are carried out in series, which has good functional group tolerance and yield

    A series of Z - [3] dendralenes and Z, Z - [3] dendralenes were synthesized

    This method has the advantages of mild reaction conditions, simple operation and high chemical selectivity, which has expanded the synthesis method of dendralenes

    This achievement was recently published in organic letters (DOI: 10.1021/acs.orglett


    The research work is mainly completed by Xia Yuntao, a 2017 level doctoral candidate of Professor Wu Lei's research group, and assisted by other graduate students and undergraduates of the research group

    Professor Wu Lei is the corresponding author of the article

    The above research work has been supported by Jiangsu Natural Science Foundation, basic scientific research business fees of central universities, Jiangsu University Blue project, and Jiangsu Province "333 high level talent training project"

    Nowadays, people and scientific research have been paid more and more attention in the economic life

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