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  1. Article ; Online: Enantioselective synthesis of spiro-

    Xie, Xiang-Qi / Li, Xingguang / Liu, Pei-Nian

    Chemical communications (Cambridge, England)

    2024  Volume 60, Issue 11, Page(s) 1448–1451

    Abstract: We present an iridium and Brønsted acid co-catalyzed enantioselective formal [4+2] cycloaddition reaction of cyclic enamides with 2-(1-hydroxyallyl)phenols. This method yields a wide range ... ...

    Abstract We present an iridium and Brønsted acid co-catalyzed enantioselective formal [4+2] cycloaddition reaction of cyclic enamides with 2-(1-hydroxyallyl)phenols. This method yields a wide range of
    Language English
    Publishing date 2024-02-01
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d3cc05923e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: On-Surface Cross-Coupling Reactions.

    Xing, Guang-Yan / Zhu, Ya-Cheng / Li, Deng-Yuan / Liu, Pei-Nian

    The journal of physical chemistry letters

    2023  Volume 14, Issue 19, Page(s) 4462–4470

    Abstract: On-surface synthesis, as a bottom-up synthetic method, has been proven to be a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials over the past 15 years. This method relies on covalent coupling reactions that occur ... ...

    Abstract On-surface synthesis, as a bottom-up synthetic method, has been proven to be a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials over the past 15 years. This method relies on covalent coupling reactions that occur on solid substrates such as metal or metal oxide surfaces under ultra-high-vacuum conditions, and the achievements with this method have greatly enriched fundamental science and technology. However, due to the complicated reactivity of organic groups, distinct diffusion of reactants and intermediates, and irreversibility of covalent bonds, achieving the high selectivity of covalent coupling reactions on surfaces remains a great challenge. As a result, only a few on-surface covalent coupling reactions, mainly involving dehalogenation and dehydrogenation homocoupling, are frequently used in the synthesis of low-dimensional carbon nanosystems. In this Perspective, we focus on the development and synthetic applications of on-surface cross-coupling reactions, mainly Ullmann, Sonogashira, Heck, and divergent cross-coupling reactions.
    Language English
    Publishing date 2023-05-08
    Publishing country United States
    Document type Journal Article ; Review
    ISSN 1948-7185
    ISSN (online) 1948-7185
    DOI 10.1021/acs.jpclett.3c00344
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Rhodium-Catalyzed 1,4-Aryl Rearrangement of Sulfur Ylide for the Synthesis of 2-Pyridyl Thioethers.

    Wang, Jie / Li, Qing-Yang / Wang, Shan-Shan / Wu, Xin-Yan / Li, Xingguang / Liu, Pei-Nian

    Organic letters

    2023  Volume 25, Issue 4, Page(s) 703–707

    Abstract: We report a novel rhodium-catalyzed rearrangement involving N-substituted 2-thiopyridones and diazoesters. This reaction proceeds through the rhodium-catalyzed formation of sulfur ylides, followed by a direct C-N bond cleavage to achieve N-to-C 1,4- ... ...

    Abstract We report a novel rhodium-catalyzed rearrangement involving N-substituted 2-thiopyridones and diazoesters. This reaction proceeds through the rhodium-catalyzed formation of sulfur ylides, followed by a direct C-N bond cleavage to achieve N-to-C 1,4-pyridyl migration. The protocol can be used to construct various thiopyridines possessing tetrasubstituted carbon stereocenters in moderate to excellent yields, which expands the transformation pattern of sulfur ylide intermediates in rearrangement reactions.
    Language English
    Publishing date 2023-01-23
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c00068
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Pd-Catalyzed Direct C-H Activation for the C5-Olefination of Methyleneindolinones.

    Xu, Xian-Kuan / Liu, Jian-Wei / Li, Deng-Yuan / Liu, Pei-Nian

    The Journal of organic chemistry

    2021  Volume 86, Issue 10, Page(s) 7288–7295

    Abstract: The direct C-H activation without directing groups can realize ... ...

    Abstract The direct C-H activation without directing groups can realize the
    MeSH term(s) Catalysis ; Kinetics ; Ligands ; Palladium
    Chemical Substances Ligands ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2021-05-06
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c00637
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives.

    Wang, Jie / Wang, Shan-Shan / Xiao, Jun / He, Yu-Jie / Wu, Xin-Yan / Li, Xingguang / Liu, Pei-Nian

    Chemical communications (Cambridge, England)

    2023  Volume 59, Issue 83, Page(s) 12495–12498

    Abstract: ... ...

    Abstract CF
    Language English
    Publishing date 2023-10-17
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d3cc03950a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Pd-Catalyzed Direct C–H Activation for the C5-Olefination of Methyleneindolinones

    Xu, Xian-Kuan / Liu, Jian-Wei / Li, Deng-Yuan / Liu, Pei-Nian

    Journal of organic chemistry. 2021 May 06, v. 86, no. 10

    2021  

    Abstract: The direct C–H activation without directing groups can realize the para-selectivity, which is a powerful and concise approach for functionalization of arenes. Utilizing the strategy, a C5-olefination of methyleneindolinones has been successfully ... ...

    Abstract The direct C–H activation without directing groups can realize the para-selectivity, which is a powerful and concise approach for functionalization of arenes. Utilizing the strategy, a C5-olefination of methyleneindolinones has been successfully developed by palladium-catalyzed direct C–H activation, which provides an expeditious access to 5-vinylindolin-2-ones with high regioselectivity. The protocol is distinguished by a mild reaction system avoiding ligand and high temperature. The kinetic isotope experiments indicate that the C–H bond cleavage is the rate-limiting step.
    Keywords aromatic hydrocarbons ; carbon-hydrogen bond activation ; cleavage (chemistry) ; isotopes ; ligands ; organic chemistry ; reaction kinetics ; regioselectivity ; temperature
    Language English
    Dates of publication 2021-0506
    Size p. 7288-7295.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c00637
    Database NAL-Catalogue (AGRICOLA)

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  7. Article ; Online: Two-Dimensional Nonbenzenoid Heteroacene Crystals Synthesized via In-Situ Embedding of Ladder Bipyrazinylenes on Au(111).

    Wang, Ying / Gong, Wen-Wen / Zhao, Yan / Xing, Guang-Yan / Kang, Li-Xia / Sha, Feng / Huang, Zheng-Yang / Liu, Jian-Wei / Han, Yan-Jie / Li, Peng / Li, Deng-Yuan / Liu, Pei-Nian

    Angewandte Chemie (International ed. in English)

    2024  Volume 63, Issue 11, Page(s) e202318142

    Abstract: Precisely introducing topological defects is an important strategy in nanographene crystal engineering because defects can tune π-electronic structures and control molecular assemblies. The synergistic control of the synthesis and assembly of ... ...

    Abstract Precisely introducing topological defects is an important strategy in nanographene crystal engineering because defects can tune π-electronic structures and control molecular assemblies. The synergistic control of the synthesis and assembly of nanographenes by embedding the topological defects to afford two-dimensional (2D) crystals on surfaces is still a great challenge. By in-situ embedding ladder bipyrazinylene (LBPy) into acene, the narrowest nanographene with zigzag edges, we have achieved the precise preparation of 2D nonbenzenoid heteroacene crystals on Au(111). Through intramolecular electrocyclization of o-diisocyanides and Au adatom-directed [2+2] cycloaddition, the nonbenzenoid heteroacene products are produced with high chemoselectivity, and lead to the molecular 2D assembly via LBPy-derived interlocking hydrogen bonds. Using bond-resolved scanning tunneling microscopy, we determined the atomic structures of the nonbenzenoid heteroacene product and diverse organometallic intermediates. The tunneling spectroscopy measurements revealed the electronic structure of the nonbenzenoid heteroacene, which is supported by density functional theory (DFT) calculations. The observed distinct organometallic intermediates during progression annealing combined with DFT calculations demonstrated that LBPy formation proceeds via electrocyclization of o-diisocyanides, trapping of heteroarynes by Au adatoms, and stepwise elimination of Au adatoms.
    Language English
    Publishing date 2024-02-06
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202318142
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Tuning Vinylethylene Carbonates into [4 + 2] Cycloaddition via Silylation and Vinylogous Peterson Elimination.

    Feng, Wei / Xu, Li / Li, Deng-Yuan / Liu, Pei-Nian

    Organic letters

    2020  Volume 22, Issue 13, Page(s) 5094–5098

    Abstract: Vinylethylene carbonates have been extensively used to trigger [3 + ...

    Abstract Vinylethylene carbonates have been extensively used to trigger [3 +
    Language English
    Publishing date 2020-06-17
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.0c01690
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Post-Functionalization of Supramolecular Polymers on Surface and the Chiral Assembly-Induced Enantioselective Reaction.

    Li, Deng-Yuan / Zhu, Ya-Cheng / Li, Shi-Wen / Shu, Chen-Hui / Liu, Pei-Nian

    Angewandte Chemie (International ed. in English)

    2021  Volume 60, Issue 20, Page(s) 11370–11377

    Abstract: Although post-functionalization is extensively used to introduce diverse functional groups into supramolecular polymers (SPs) in solution, post-functionalization of SPs on surfaces still remains unexplored. Here we achieved the on-surface post- ... ...

    Abstract Although post-functionalization is extensively used to introduce diverse functional groups into supramolecular polymers (SPs) in solution, post-functionalization of SPs on surfaces still remains unexplored. Here we achieved the on-surface post-functionalization of two SPs derived from 5,10,15-tri-(4-pyridyl)-20-bromophenyl porphyrin (Br-TPyP) via cross-coupling reactions on Au(111). The ladder-shaped, Cu-coordinated SPs preformed from Br-TPyP were functionalized through Heck reaction with 4-vinyl-1,1'-biphenyl. In the absence of Cu, Br-TPyP formed chiral SPs as two enantiomers via self-assembly, which were functionalized via divergent cross-coupling reaction with 4-isocyano-1,1'-biphenyl (ICBP). Surprisingly, this reaction was discovered as an enantioselective on-surface reaction induced by the chirality of SPs. Mechanistic analysis and DFT calculations indicated that after debromination of Br-TPyP and the first addition of ICBP, only one attack direction of ICBP to the chiral SP intermediate is permissive in the second addition step due to the steric hindrance, which guaranteed the high enantioselectivity of the reaction.
    Language English
    Publishing date 2021-04-07
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202016395
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Heterobicyclic Core Retained Hydroarylations through C-H Activation: Synthesis of Epibatidine Analogues.

    Li, Deng-Yuan / Huang, Zheng-Lu / Liu, Pei-Nian

    Organic letters

    2018  Volume 20, Issue 7, Page(s) 2028–2032

    Abstract: The heterobicyclic core retained hydroarylation of oxa/azabenzonorbornadienes with quinoline N-oxides has been achieved under rhodium catalysis, giving quinoline N-oxide substituted heterobicyclic structures with excellent regioselectivity and in good ... ...

    Abstract The heterobicyclic core retained hydroarylation of oxa/azabenzonorbornadienes with quinoline N-oxides has been achieved under rhodium catalysis, giving quinoline N-oxide substituted heterobicyclic structures with excellent regioselectivity and in good yields. As the first example of the direct introduction of quinoline N-oxides onto heterobicyclic structures, the strained heterobicyclic core was well retained in the reaction. The products could be successfully transformed into a series of useful compounds, including epibatidine analogues.
    Language English
    Publishing date 2018--06
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.8b00571
    Database MEDical Literature Analysis and Retrieval System OnLINE

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