One-pot multicoupling reaction of silylcopper reagents, organolithium compounds and α,β-unsaturated nitriles

被引:5
作者
Pulido, Francisco J. [1 ]
Barbero, Asuncion [1 ]
Blanco, Yolanda [1 ]
机构
[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain
关键词
DOUBLE NUCLEOPHILIC-ADDITION; DIMETALLIC ORGANIC-COMPOUNDS; ORGANOZINC COMPOUNDS; ZINC; ALLENE; CYCLOPENTANE; ALLYLSILANES; OXIDATION; COPPER; SCOPE;
D O I
10.1039/c0ob00775g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The silylcupration of allene using a lower order silylcopper species gives an allylsilane-vinyl copper intermediate 2 which, in conjunction with an organolithium reagent, is able to participate in a one-pot multicoupling reaction with alpha,beta-unsaturated nitriles. The scope of this tandem reaction is studied and a possible mechanism pathway is outlined.
引用
收藏
页码:1454 / 1458
页数:5
相关论文
共 50 条
  • [21] One-pot oxidative Mannich-type reaction of lactams with alkyl malonates
    Matsuo, Jun-ichi
    Tanaki, Yumi
    Ishibashi, Hiroyuki
    [J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3233 - 3236
  • [22] Metalloporphyrin-based multifunctional catalysts for one-pot assisted Tandem reaction
    da Silva Junior, Renaldo Marcos
    dos Santos, Everton Henrique
    Nakagaki, Shirley
    [J]. MOLECULAR CATALYSIS, 2023, 541
  • [23] Development of one-pot Cu/cellulose derived carbon catalysts for RWGS reaction
    Tarifa, P.
    Gonzalez-Castano, M.
    Cazana, F.
    Monzon, A.
    Arellano-Garcia, H.
    [J]. FUEL, 2022, 319
  • [24] New One-Pot Synthesis of Catechol Thioethers Based on H2S and Unsaturated Hydrocarbons
    Burmistrova, Daria
    Smolyaninov, Ivan
    Berberova, Nadezhda
    Eremenko, Igor
    [J]. CHEMISTRYSELECT, 2020, 5 (45): : 14515 - 14519
  • [25] Trichloroisocyanuric acid mediated one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones
    Bhatt, Ashish
    Singh, Rajesh K.
    Kant, Ravi
    [J]. SYNTHETIC COMMUNICATIONS, 2019, 49 (08) : 1083 - 1091
  • [26] A one-pot procedure for methylenating carbonyl compounds using the Nysted reagent and titanocene dichloride
    Haahr, Adam
    Rankovic, Zoran
    Hartley, Richard C.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (23) : 3020 - 3022
  • [27] A one-pot oxidation/allylation/oxidation sequence for the preparation of β,γ-unsaturated ketones directly from primary alcohols
    Moody, Catherine L.
    Pugh, David S.
    Taylor, Richard J. K.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (19) : 2511 - 2514
  • [28] An Efficient One-Pot Synthesis of Nitriles from Alcohols or Aldehydes with NH3 Catalyzed by a Supported Ruthenium Hydroxide
    Oishi, Takamichi
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    [J]. TOPICS IN CATALYSIS, 2010, 53 (7-10) : 479 - 486
  • [29] Synthesis of Biopolymer-Derived Zirconium Carbide Powder by Facile One-Pot Reaction
    Patra, Niranjan
    Jayaseelan, Daniel Doni
    Lee, William Edward
    [J]. JOURNAL OF THE AMERICAN CERAMIC SOCIETY, 2015, 98 (01) : 71 - 77
  • [30] A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols
    Hou, Xufeng
    Jing, Zhenzhong
    Bai, Xiangbin
    Jiang, Zhiyong
    [J]. MOLECULES, 2016, 21 (07)