Palladium-Catalyzed Alkene Carboalkoxylation Reactions of Phenols and Alcohols for the Synthesis of Carbocycles

被引:16
|
作者
White, Derick R. [1 ]
Herman, Madeline I. [1 ]
Wolfe, John P. [1 ]
机构
[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48109 USA
关键词
MITSUNOBU REACTION; CARBOAMINATION REACTIONS; ACTIVE CATALYST; ARYL ETHERS; ALKYL-ARYL; DIFUNCTIONALIZATION; AMINATION; OXIDATION;
D O I
10.1021/acs.orglett.7b01975
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intermolecular alkene difunctionalization reactions between terminal alkenes bearing a pendant aryl or alkenyl triflate electrophile and exogenous alcohol or phenol nucleophiles are described. These transformations afford substituted indanyl or alkylidenecyclopentyl ethers in high yield with excellent diastereoselectivity. The transformations proceed through intermolecular capture of an intermediate [pd(II)-alkene]+[OTf](-) complex by the alcohol or phenol nucleophile.
引用
收藏
页码:4311 / 4314
页数:4
相关论文
共 50 条
  • [31] Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions
    Hu, Naifu
    Li, Ke
    Wang, Zheng
    Tang, Wenjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (16) : 5044 - 5048
  • [32] Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles
    Peterson, Luke J.
    Wolfe, John P.
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2339 - 2344
  • [33] Palladium-catalyzed cocyclotrimerization of arynes with a pyramidalized alkene
    Alonso, Jose M.
    Quiroga, Sabela
    Codony, Sandra
    Turcu, Andreea L.
    Barniol-Xicota, Marta
    Perez, Dolores
    Guitian, Enrique
    Vazquez, Santiago
    Pena, Diego
    CHEMICAL COMMUNICATIONS, 2018, 54 (47) : 5996 - 5999
  • [34] Palladium-catalyzed aryl-acylation of alkene
    Yamane, M
    Kubota, Y
    Narasaka, K
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (8-9) : 2105 - 2105
  • [35] Development of aliphatic alcohols as nucleophiles for palladium-catalyzed DYKAT reactions: Total synthesis of (+)-hippospongic acid A
    Trost, BM
    Machacek, MR
    Tsui, HC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) : 7014 - 7024
  • [36] Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
    Xu, Jingxiu
    Sun, Jing
    Zhao, Jinwu
    Huang, Bin
    Li, Xiaohan
    Sun, Yulun
    RSC ADVANCES, 2017, 7 (58): : 36242 - 36245
  • [38] Palladium-catalyzed etherification of allyl alcohols using phenols in the presence of titanium(IV) isopropoxide
    Satoh, T
    Ikeda, M
    Miura, M
    Nomura, M
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14): : 4877 - 4879
  • [39] Palladium-catalyzed silylation of alcohols with hexamethyldisilane
    Shirakawa, Eiji
    Hironaka, Koji
    Otsuka, Hidehito
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2006, (37) : 3927 - 3929
  • [40] Palladium-Catalyzed Aminocarbonylation of Allylic Alcohols
    Li, Haoquan
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (29) : 10050 - 10056