Synthesis of Allenes via Gold-Catalyzed Intermolecular Reaction of Propargylic Alcohols and Aromatic Compounds

被引:40
|
作者
Xu, Cheng-Fu [1 ]
Xu, Mei [1 ]
Yang, Liu-Qing [1 ]
Li, Chuan-Ying [1 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 1,3-DISUBSTITUTED ALLENES; OLEFINATION; SUBSTITUTION; ALDEHYDES; INDOLES; COMPLEX; KETONES; ALKYNES;
D O I
10.1021/jo300147u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.
引用
收藏
页码:3010 / 3016
页数:7
相关论文
共 50 条
  • [21] Accessing chemical diversity by stereoselective gold-catalyzed manipulation of allylic and propargylic alcohols
    Cera, Gianpiero
    Chiarucci, Michel
    Bandini, Marco
    PURE AND APPLIED CHEMISTRY, 2012, 84 (08) : 1673 - 1684
  • [22] Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes
    Hosseyni, Seyedmorteza
    Smith, Courtney A.
    Shi, Xiaodong
    ORGANIC LETTERS, 2016, 18 (24) : 6336 - 6339
  • [23] Gold-catalyzed highly enantioselective synthesis of axially chiral allenes
    Lo, Vanessa Kar-Yan
    Wong, Man-Kin
    Che, Chi-Ming
    ORGANIC LETTERS, 2008, 10 (03) : 517 - 519
  • [24] A Reaction Mechanism for Gold-Catalyzed Hydroamination/Cyclization of o-Phenylendiamine and Propargylic Alcohols. A DFT Study
    Wang, Yueyue
    Ling, Baoping
    Liu, Peng
    Bi, Siwei
    ORGANOMETALLICS, 2018, 37 (18) : 3035 - 3044
  • [25] Gold-catalyzed fluorination of alkynes/allenes: mechanistic explanations and reaction scope
    Roy, Deblina Singha
    Tanwer, Yogesh Bhaskar Singh
    Patra, Snigdha Rani
    Kumar, Shivam
    Bhunia, Sabyasachi
    Das, Debjit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 23 (01) : 11 - 35
  • [26] Ruthenium-catalyzed enantioselective prolpargylation of aromatic compounds with propargylic alcohols via allenylidene intermediates
    Matsuzawa, Hiroshi
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) : 6488 - 6491
  • [27] Gold(I)-Catalyzed Synthesis of Heterocycles via Allene Oxide from Propargylic Alcohols
    Bera, Nabakumar
    Lenka, Bhabani Sankar
    Bishi, Sangita
    Samanta, Shantanu
    Sarkar, Debayan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9729 - 9754
  • [28] Gold-catalyzed intermolecular hydroamination of allenes: First example of the use of an aliphatic amine in hydroamination
    Nishina, Naoko
    Yamamoto, Yoshinori
    SYNLETT, 2007, (11) : 1767 - 1770
  • [29] Gold-Catalyzed Propargylic Substitution Followed by Cycloisomerization in Ionic Liquid: Environmentally Friendly Synthesis of Polysubstituted Furans from Propargylic Alcohols and 1,3-Dicarbonyl Compounds
    Chiaki, Hitomi
    Hashimoto, Yoshimitsu
    Morita, Nobuyoshi
    MOLECULES, 2024, 29 (22):
  • [30] Propargylation of aromatic compounds with propargylic alcohols catalyzed by a cationic diruthenium complex
    Nishibayashi, Y
    Inada, Y
    Yoshikawa, M
    Hidai, M
    Uemura, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (13) : 1495 - 1498