Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols

被引：11
|
作者：
Ma, Xiantao [1 ]
Yu, Jing [1 ]
Ma, Ruitian [1 ]
Yan, Ran [1 ]
Zhang, Zhenlei [1 ,2 ]
机构：
[1] Xinyang Normal Univ, Coll Chem & Chem Engn, Xinyang 464000, Peoples R China
[2] Fuyang Normal Univ, Sch Chem & Mat Engn, Fuyang 236037, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 39卷 / 03期
关键词：
stabilized phosphorus ylides; allylic alcohols; dehydrative cross couplings; palladium catalysis; BAYLIS-HILLMAN REACTION; SKIPPED DIENES; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; SUBSTITUTION; ALLYLATION; EFFICIENT; NICKEL; ACTIVATION; ALKYLATION;
D O I：
10.6023/cjoc201812051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A dehydrative cross coupling of ketone-stabilized phosphorus ylides with the readily available allylic alcohols followed by an one-pot Wittig reaction is developed. A range of functional 1,4-dienes could be obtained in 52%similar to 95% isolated yields in the presence of 5 mol% Pd(PPh3)(4) and 20 mol% B(OH)(3). The same method can be extended to ester or nitrile-stabilized phosphorus ylides, affording the corresponding 1,4-dienes in moderate yields.
引用
收藏
页码：830 / 835
页数：6
相关论文
共 54 条
  • [1] Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper-Catalyzed Enantioselective Synthesis of 1,4-Dienes Containing Z or E Alkenes
    Akiyama, Katsuhiro
    Gao, Fang
    Hoveyda, Amir H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) : 419 - 423
  • [2] Allylic Alcohols: Sustainable Sources for Catalytic Enantioselective Alkylation Reactions
    Bandini, Marco
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 994 - 995
  • [3] The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes
    Basavaiah, D
    Sharada, DS
    Kumaragurubaran, N
    Reddy, RM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7135 - 7137
  • [4] Baylis-Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes
    Basavaiah, D
    Kumaragurubaran, N
    Sharada, DS
    [J]. TETRAHEDRON LETTERS, 2001, 42 (01) : 85 - 87
  • [5] Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates
    Butt, Nicholas A.
    Zhang, Wanbin
    [J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) : 7929 - 7967
  • [6] Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates
    Chen, Xiaoyi
    Chen, Dongxu
    Lu, Zenghui
    Kong, Lichun
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6338 - 6343
  • [7] Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity
    Cornella, Josep
    Zarate, Cayetana
    Martin, Ruben
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (23) : 8081 - 8097
  • [8] Edmonds M., 2004, MODERN CARBONYL OLEF, P1
  • [9] Tsuji-Trost Type Functionalization of Allylic Substrates with Challenging Leaving Groups: Recent Developments
    Ferraccioli, Raffaella
    Pignataro, Luca
    [J]. CURRENT ORGANIC CHEMISTRY, 2015, 19 (02) : 106 - 120
  • [10] Total synthesis of iejimalide A-D and assessment of the remarkable actin-depolymerizing capacity of these polyene macrolides
    Fuerstner, Alois
    Nevado, Cristina
    Waser, Mario
    Tremblay, Martin
    Chevrier, Carine
    Teply, Filip
    Aiessa, Christophe
    Moulin, Emilie
    Mueller, Oliver
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) : 9150 - 9161
123456