Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

被引:26
作者
Beaulieu, Louis-Philippe B. [1 ]
Roman, Daniela Sustac [1 ]
Vallee, Frederic [1 ]
Charette, Andre B. [1 ]
机构
[1] Univ Montreal, FRQNT Ctr Green Chem & Catalysis, Dept Chem, Stn Downtown, Montreal, PQ H3C 3J7, Canada
基金
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词
CATALYZED DIRECT ARYLATION; POTASSIUM TERT-BUTOXIDE; C-H ACTIVATION; ARYL HALIDES; RADICAL ISOMERIZATION; COUPLING REACTIONS; IPSO SUBSTITUTION; TRANSLOCATION; COMPLEXES; NITROGEN;
D O I
10.1039/c2cc33547f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)(4) and NaHMDS. Mechanistic investigations support the catalytic nature of Ni-0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.
引用
收藏
页码:8249 / 8251
页数:3
相关论文
共 26 条
  • [1] Anslyn E. V., 2006, MODERN PHYS ORGANIC
  • [2] Ashby N. R. E. C., 1981, J ORG CHEM, V46, P2429
  • [3] Synthesis using aromatic homolytic substitution - recent advances
    Bowman, W. Russell
    Storey, John M. D.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) : 1803 - 1822
  • [4] OXIDATIVE ADDITIONS OF ARYL, VINYL, AND ACYL HALIDES TO TRIETHYLPHOSPHINENICKEL(O) COMPLEXES
    FAHEY, DR
    MAHAN, JE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) : 2501 - 2508
  • [5] LEE E, 1993, TETRAHEDRON LETT, V34, P2343
  • [6] RADICAL ISOMERIZATION VIA INTRAMOLECULAR IPSO SUBSTITUTION OF N-ARYLAMIDES - ARYL TRANSLOCATION FROM NITROGEN TO CARBON
    LEE, E
    WHANG, HS
    CHUNG, CK
    [J]. TETRAHEDRON LETTERS, 1995, 36 (06) : 913 - 914
  • [7] The Catalytic Ability of Various Transition Metals in the Direct Functionalization of Aromatic C-H Bonds
    Li, Hu
    Sun, Chang-Liang
    Yu, Miao
    Yu, Da-Gang
    Li, Bi-Jie
    Shi, Zhang-Jie
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (13) : 3593 - 3597
  • [8] Cobalt-Catalyzed Direct Arylation of Unactivated Arenes with Aryl Halides
    Liu, Wei
    Cao, Hao
    Xin, Jie
    Jin, Liqun
    Lei, Aiwen
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (13) : 3588 - 3592
  • [9] Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C-H Arylation of Unactivated Benzene
    Liu, Wei
    Cao, Hao
    Zhang, Hua
    Zhang, Heng
    Chung, Kin Ho
    He, Chuan
    Wang, Haibo
    Kwong, Fuk Yee
    Lei, Aiwen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) : 16737 - 16740
  • [10] Iron-Catalyzed Direct Arylation of Unactivated Arenes with Aryl Halides
    Liu, Wei
    Cao, Hao
    Lei, Aiwen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) : 2004 - 2008