Ni-Catalyzed Allylic Dearomatization Reaction of β-Naphthols with Allylic Alcohols

被引:25
作者
Zhang, Hui-Jun [1 ]
Gu, Qing [2 ]
You, Shu-Li [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
国家重点研发计划;
关键词
CROSS-COUPLING REACTIONS; ASYMMETRIC DEAROMATIZATION; GRIGNARD-REAGENTS; ENANTIOSELECTIVE DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; SUBSTITUTION-REACTIONS; BOND FORMATION; ALKYLATION; ALLYLATION; PALLADIUM;
D O I
10.1021/acs.orglett.0c01109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ni-catalyzed intermolecular allylic dearomatization reaction of beta-naphthols with allylic alcohols was achieved. By utilizing Ni(cod)(2) as a catalyst precursor, DPEphos as a ligand and 4 angstrom molecular sieves as additives, the dearomatization reaction of beta-naphthols with aryl allylic alcohols proceeded smoothly under mild conditions, affording the desired beta-naphthalenone products bearing a quaternary carbon center in moderate to good yields with excellent linear selectivity.
引用
收藏
页码:3297 / 3301
页数:5
相关论文
共 63 条
  • [1] Nickel-Catalyzed α-Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols
    Bernhard, Yann
    Thomson, Brodie
    Ferey, Vincent
    Sauthier, Mathieu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) : 7460 - 7464
  • [2] Nickel-Catalysed Bis-Allylation of Activated Nucleophiles with Allyl Alcohol
    Blieck, Remi
    Azizi, Mohamed Salah
    Mifleur, Alexis
    Roger, Maxime
    Persyn, Clement
    Sauthier, Mathieu
    Bonin, Helene
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (06) : 1194 - 1198
  • [3] Further developments in metal-catalysed C-C bond cleavage in allylic dimethyl malonate derivatives
    Bricout, H
    Carpentier, JF
    Mortreux, A
    [J]. TETRAHEDRON LETTERS, 1997, 38 (06) : 1053 - 1056
  • [4] Bis(aminophosphine)-nickel complexes as efficient catalysts for alkylation of allylic acetates with stabilized nucleophiles
    Bricout, H
    Carpentier, JF
    Mortreux, A
    [J]. TETRAHEDRON LETTERS, 1996, 37 (34) : 6105 - 6108
  • [5] NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC COMPOUNDS WITH SOFT NUCLEOPHILES - AN EFFICIENT ALTERNATIVE TO PALLADIUM CATALYSIS
    BRICOUT, H
    CARPENTIER, JF
    MORTREUX, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) : 1863 - 1864
  • [6] Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode
    Chau, Stephen T.
    Lutz, J. Patrick
    Wu, Kevin
    Doyle, Abigail G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9153 - 9156
  • [7] Chemo-, Diastereo-, and Enantioselective Iridium-Catalyzed Allylic Intramolecular Dearomatization Reaction of Naphthol Derivatives
    Cheng, Qiang
    Wang, Ye
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) : 3496 - 3499
  • [8] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds
    Cherney, Alan H.
    Kadunce, Nathaniel T.
    Reisman, Sarah E.
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9587 - 9652
  • [9] CARBON - CARBON BOND FORMATION IN DICHLOROBIS(TRIPHENYLPHOSPHINE)NICKEL-CATALYSED REACTION BETWEEN GRIGNARD REAGENTS AND ALLYLIC ALCOHOLS
    CHUIT, C
    FELKIN, H
    FRAJERMA.C
    ROUSSI, G
    SWIERCZE.G
    [J]. CHEMICAL COMMUNICATIONS, 1968, (24) : 1604 - &
  • [10] Nickel(0)-catalysed asymmetric cross-coupling reactions of allylic compounds with Grignard reagents using optically active oxazolinylferrocenylphosphines as ligands
    Chung, KG
    Miyake, Y
    Uemura, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16): : 2725 - 2729