A Direct BrOnsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates

被引：8
|
作者：
Regier, Jeffery [1 ]
Maillet, Robert [2 ]
Bolshan, Yuri [1 ]
机构：
[1] Univ Ontario Inst Technol, Fac Sci, 2000 Simcoe St North, Oshawa, ON L1H 7K4, Canada
[2] Univ Ottawa, Fac Med, 451 Smyth Rd, Ottawa, ON K1H 8M5, Canada
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 13期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Azidation; Benzhydrol; Carbohydrates; BrOnsted acid; BENZYL ALCOHOLS; AZIDES; ALLYLATION; CONVERSION; CHLORIDE;
D O I：
10.1002/ejoc.201900104
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a BrOnsted acid HBF4OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron-donating and electron-withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well-tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.
引用
收藏
页码：2390 / 2396
页数：7
相关论文
共 50 条
  • [21] Bronsted acid-catalyzed desymmetrization of meso-aziridines
    Rowland, Emily B.
    Rowland, Gerald B.
    Rivera-Otero, Edwin
    Antilla, Jon C.
    Journal of the American Chemical Society, 2007, 129 (40): : 12084 - 12085
  • [22] Bronsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide
    Cioc, Razvan C.
    Schuckman, Peter
    Preschel, Hans D.
    Vlaar, Tjostil
    Ruijter, Eelco
    Orru, Romano V. A.
    ORGANIC LETTERS, 2016, 18 (15) : 3562 - 3565
  • [23] Enantioselective PCCP Bronsted acid-catalyzed aminalization of aldehydes
    Kamlar, Martin
    Reiberger, Robert
    Nigrini, Martin
    Cisarova, Ivana
    Vesely, Jan
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2433 - 2440
  • [24] Bronsted acid-catalyzed desymmetrization of meso-aziridines
    Rowland, Emily B.
    Rowland, Gerald B.
    Rivera-Otero, Edwin
    Antilla, Jon C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) : 12084 - +
  • [25] Bronsted Acid-Catalyzed Dihydroxylation of Olefins in Aqueous Medium
    Rosatella, Andreia A.
    Afonso, Carlos A. M.
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2920 - 2926
  • [26] Bronsted Acid-Catalyzed Dipeptides Functionalization through Azlactones
    dos Santos, Igor F.
    de Castro, Pedro P.
    de Almeida, Angelina M.
    Amarante, Giovanni W.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2017, 28 (07) : 1145 - 1148
  • [27] A general Bronsted acid-catalyzed allylation of benzhydryl alcohols
    Orizu, Ifedi
    Solshan, Yuri
    TETRAHEDRON LETTERS, 2016, 57 (51) : 5798 - 5800
  • [28] Bronsted acid-catalyzed chlorination of aromatic carboxylic acids
    Yu, Zhiqun
    Yao, Hongmiao
    Xu, Qilin
    Liu, Jiming
    Le, Xingmao
    Ren, Minna
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2021, 196 (08) : 685 - 689
  • [29] Direct Bronsted acid-catalyzed derivatization of cellulose with poly(L-lactic acid) and D-mandelic acid
    Hafren, Jonas
    Cordova, Armando
    NORDIC PULP & PAPER RESEARCH JOURNAL, 2007, 22 (02) : 184 - 187
  • [30] Exploiting hexafluoroisopropanol (HFIP) in Lewis and Bronsted acid-catalyzed reactions
    Pozhydaiev, Valentyn
    Power, Martin
    Gandon, Vincent
    Moran, Joseph
    Leboeuf, David
    CHEMICAL COMMUNICATIONS, 2020, 56 (78) : 11548 - 11564
12345