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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 05期
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
  • [1] SEQUENTIAL ONE-POT REACTIONS OF THIOFORMAMIDES WITH ORGANOLITHIUM AND ZINC REAGENTS
    Murai, Toshiaki
    Matsushita, Koji
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (05) : 1094 - 1103
  • [2] Asymmetric One-Pot Conjugate Addition of Grignard Reagents to α,β-Unsaturated Compounds Followed by Reaction with Carbenium Ions
    Drusan, Michal
    Rakovsky, Erik
    Marek, Jaromir
    Sebesta, Radovan
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (07) : 1493 - 1498
  • [3] One-pot synthesis of polyfunctionalized α,β-unsaturated nitriles from nitroalkanes
    Ballini, R
    Fiorini, D
    Gil, MV
    Palmieri, A
    TETRAHEDRON LETTERS, 2003, 44 (50) : 9033 - 9034
  • [4] Practical Synthesis of (Z)-α,β-Unsaturated Nitriles via a One-Pot Sequential Hydroformylation/Knoevenagel Reaction
    Jiang, Yanxin
    Li, Chao
    Tang, Songbai
    Tao, Shaokun
    Yuan, Maolin
    Li, Ruixiang
    Chen, Hua
    Fu, Haiyan
    Zheng, Xueli
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15413 - 15422
  • [5] The one-pot Wittig reaction:: A facile synthesis of α,β-unsaturated esters and nitriles by using nanocrystalline magnesium oxide
    Choudary, Boyapati M.
    Mahendar, Koosam
    Kantam, M. Lakshmi
    Ranganath, Kalluri V. S.
    Athar, Taimur
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) : 1977 - 1985
  • [6] ONE-POT TRANSFORMATION OF KETONES TO ALPHA,BETA-UNSATURATED NITRILES VIA TRIMETHYLSILOXY NITRILES
    ODA, M
    YAMAMURO, A
    WATABE, T
    CHEMISTRY LETTERS, 1979, (12) : 1427 - 1430
  • [7] One-pot tandem catalytic synthesis of α, β-unsaturated nitriles from alcohol with nitriles in aqueous phase
    Chen, Chen
    Yang, Hanmin
    Chen, Jizhong
    Zhang, Ran
    Guo, Li
    Gan, Huimei
    Song, Baoning
    Zhu, Wenwen
    Hua, Li
    Hou, Zhenshan
    CATALYSIS COMMUNICATIONS, 2014, 47 : 49 - 53
  • [8] One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds
    Sugiura, Masaharu
    Ashikari, Yasuhiko
    Nakajima, Makoto
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8830 - 8835
  • [9] SYNTHESIS OF ENAMIDINES BY REACTION OF ORGANOLITHIUM COMPOUNDS WITH NITRILES
    COOK, LS
    WAKEFIELD, BJ
    TETRAHEDRON LETTERS, 1976, (02) : 147 - 150
  • [10] One-Pot Reductive Mono-N-alkylation of Aromatic Nitro Compounds Using Nitriles as Alkylating Reagents
    Neogi, Subhasish
    Naskar, Dinabandhu
    SYNTHETIC COMMUNICATIONS, 2011, 41 (13) : 1901 - 1915
12345