A general Bronsted acid-catalyzed allylation of benzhydryl alcohols

被引:12
|
作者
Orizu, Ifedi [1 ]
Solshan, Yuri [2 ]
机构
[1] Univ Arkansas, 345 N Campus Dr, Fayetteville, AR 72701 USA
[2] UOIT, 2000 Simcoe St North, Oshawa, ON L1H 7K4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Bronsted acid; Allylation; Benzhydryl alcohol; Catalysis; Metal-free; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ALCOHOLS; BENZYLIC ALCOHOLS; COUPLING REACTIONS; LEWIS-ACID; ALLYLTRIMETHYLSILANE; ALLYLSILANES; ETHERS; ALKYLATION; EFFICIENT;
D O I
10.1016/j.tetlet.2016.11.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient Bronsted acid-catalyzed allylation of benzhydryl alcohols has been developed. The reaction occurs within 5 min in the presence of sub-stoichiometric amounts of HBF4 center dot OEt2 to afford the desired products in good to excellent yields. A variety of functional groups were tolerated under the developed conditions including amides, aldehydes, hydroxyl and carboxylic acid. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5798 / 5800
页数:3
相关论文
共 50 条
  • [21] Lewis and Bronsted acid-catalyzed allylsilane oligomerization
    Wigman, Benjamin
    Franz, Annaliese
    Armstrong, Brittany
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [22] Bronsted acid-catalyzed amidation of imines.
    Antilla, JC
    Zhang, H
    Wang, Y
    Rowland, EB
    Rowland, GB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U390 - U390
  • [23] Mechanism of Bronsted acid-catalyzed conversion of carbohydrates
    Yang, Gang
    Pidko, Evgeny A.
    Hensen, Emiel J. M.
    JOURNAL OF CATALYSIS, 2012, 295 : 122 - 132
  • [24] Chiral Bronsted Acid-Catalyzed Allylboration of Aldehydes
    Jain, Pankaj
    Antilla, Jon C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 11884 - 11886
  • [25] Chiral Bronsted acid-catalyzed allylboration of aldehydes
    Jain, Pankaj
    Antilla, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [26] Bronsted acid-catalyzed hydroarylation of activated olefins
    Fleischer, Ivana
    Pospech, Jola
    RSC ADVANCES, 2015, 5 (01) : 493 - 496
  • [27] Bronsted Acid-Catalyzed Intramolecular Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer
    Bunrit, Anon
    Dahlstrand, Christian
    Olsson, Sandra K.
    Srifa, Pemikar
    Huang, Genping
    Orthaber, Andreas
    Sjoberg, Per J. R.
    Biswas, Srijit
    Himo, Fahmi
    Samec, Joseph S. M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (14) : 4646 - 4649
  • [28] Bronsted acid-catalyzed intramolecular nucleophilic substitution of the hydroxyl group in stereogenic alcohols with chirality transfer
    Bunrit, Anon
    Dahlstrand, Christian
    Olsson, Sandra
    Srifa, Pemikar
    Huang, Genping
    Sjoberg, Per
    Biswas, Srijit
    Himo, Fahmi
    Samec, Joseph
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [29] Bronsted Acid Catalyzed Asymmetric Silylation of Alcohols
    Hyodo, Kengo
    Gandhi, Shikha
    van Gemmeren, Manuel
    List, Benjamin
    SYNLETT, 2015, 26 (08) : 1093 - 1095
  • [30] ACID-CATALYZED REARRANGEMENT OF HYDROPEROXIDES .I. BENZHYDRYL HYDROPEROXIDES
    ANDERSON, GH
    SMITH, JG
    CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (09): : 1553 - &