A highly effective (triphenyl phosphite)palladium catalyst for a cross-coupling reaction of allylic alcohols with organoboronic acids

被引:81
|
作者
Kayaki, Y
Koda, T
Ikariya, T
机构
[1] Tokyo Inst Technol, Grad Sch Sci & Technol, Meguro Ku, Tokyo 1528552, Japan
[2] Tokyo Inst Technol, Frontier Collaborat Res Ctr, Meguro Ku, Tokyo 1528552, Japan
[3] PRESTO, Japan Sci & Technol Agcy, Meguro Ku, Tokyo 1528552, Japan
关键词
allylation; boranes; C-C coupling; green chemistry; palladium;
D O I
10.1002/ejoc.200400621
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cross coupling reaction of aryl and vinyl boronic acids and allylic alcohols proceeded smoothly in toluene or dioxane in the presence of a (triphenyl phosphite) palladium catalyst to give the corresponding allylbenzene derivatives and 1,4-dienes. Neither cocatalysts for promoting C-O bond cleavage of allylic alcohols nor bases for activation of organoboron reagents are required for promoting the coupling process. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:4989 / 4993
页数:5
相关论文
共 50 条
  • [1] Palladium catalyzed cross-coupling reaction of organoboronic acids with β-(perfluoroalkyl)ethyl iodides
    Yang, GS
    Xie, XJ
    Zhao, G
    Ding, Y
    JOURNAL OF FLUORINE CHEMISTRY, 1999, 98 (02) : 159 - 161
  • [2] Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids
    Tsukamoto, Hirokazu
    Uchiyarna, Tomomi
    Suzuki, Takamichi
    Kondo, Yoshinori
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (16) : 3005 - 3013
  • [3] Palladium-catalyzed stereospecific cross-coupling of enantioenriched allylic alcohols with boronic acids
    Wu, Hai-Bian
    Ma, Xian-Tao
    Tian, Shi-Kai
    CHEMICAL COMMUNICATIONS, 2014, 50 (02) : 219 - 221
  • [4] Palladium-catalysed cross-coupling of organotellurium compounds with organoboronic acids
    Kang, SK
    Hong, YT
    Kim, DH
    Lee, SH
    JOURNAL OF CHEMICAL RESEARCH-S, 2001, (07): : 283 - 285
  • [5] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORONIC ACIDS WITH ORGANIC ELECTROPHILES
    MARTIN, AR
    YANG, YH
    ACTA CHEMICA SCANDINAVICA, 1993, 47 (03): : 221 - 230
  • [6] Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Organoboronic Acids
    Xia, Ying
    Ge, Rui
    Chen, Li
    Liu, Zhen
    Xiao, Qing
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 7856 - 7864
  • [7] Halide-free dehydrative allylation using allylic alcohols promoted by a palladium-triphenyl phosphite catalyst
    Kayaki, Y
    Koda, T
    Ikariya, T
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07): : 2595 - 2597
  • [8] Efficient Palladium-Catalyzed Cross-Coupling Reaction of Alkynyl Halides with Organoboronic Acids under Aerobic Conditions
    Tang, Jian-Sheng
    Tian, Mi
    Sheng, Wen-Bing
    Guo, Can-Cheng
    SYNTHESIS-STUTTGART, 2012, 44 (04): : 541 - 546
  • [9] Palladium-Catalyzed Cross-Coupling Reaction o Arenesulphonate with Phosphite
    Feng, Zhigang
    Xie, Xiaomin
    Zhang, Zhaoguo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (04) : 896 - 901
  • [10] Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids
    Zhang, Dejiang
    Le, Liyuan
    Qiu, Renhua
    Wong, Wai-Yeung
    Kambe, Nobuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 3104 - 3114