N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters

被引：182
|
作者：
Maki, Brooks E. [1 ]
Scheidt, Karl A. [1 ]
机构：
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 19期
关键词：
D O I：
10.1021/ol8018488
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.
引用
收藏
页码：4331 / 4334
页数：4
相关论文
共 50 条
  • [1] N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols
    Movassaghi, M
    Schmidt, MA
    [J]. ORGANIC LETTERS, 2005, 7 (12) : 2453 - 2456
  • [2] N-heterocyclic carbene-catalyzed oxidation of aldehydes for the synthesis of amides via phenolic esters
    Ji, Miran
    Lim, Seungyeon
    Jang, Hye-Young
    [J]. RSC ADVANCES, 2014, 4 (54) : 28225 - 28228
  • [3] N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN
    Fan, Ye-Cheng
    Du, Guang-Fen
    Sun, Wan-Fu
    Kang, Wei
    He, Lin
    [J]. TETRAHEDRON LETTERS, 2012, 53 (17) : 2231 - 2233
  • [4] N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds
    Hirano, Keiichi
    Biju, Akkattu T.
    Piel, Isabel
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14190 - +
  • [5] N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
    Ishii, Takuya
    Kakeno, Yuki
    Nagao, Kazunori
    Ohmiya, Hirohisa
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (09) : 3854 - 3858
  • [6] N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
    Gelat, Fabien
    Patra, Atanu
    Pannecoucke, Xavier
    Biju, Akkattu T.
    Poisson, Thomas
    Besset, Tatiana
    [J]. ORGANIC LETTERS, 2018, 20 (13) : 3897 - 3901
  • [7] N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
    Alanthadka, Anitha
    Maheswari, C. Uma
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1199 - 1203
  • [8] Direct and efficient N-heterocyclic carbene-catalyzed hydroxymethylation of aldehydes
    Kuhl, Nadine
    Glorius, Frank
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 573 - 575
  • [9] N-Heterocyclic Carbene-Catalyzed Redox Reactions of α-Functionalized Aldehydes
    Rong, Zi-Qiang
    Zhang, Wei
    Yang, Gui-Qiu
    You, Shu-Li
    [J]. CURRENT ORGANIC CHEMISTRY, 2011, 15 (17) : 3077 - 3090
  • [10] Formation, Oxidation, and Fate of the Breslow Intermediate in the N-Heterocyclic Carbene-Catalyzed Aerobic Oxidation of Aldehydes
    Bortolini, Olga
    Chiappe, Cinzia
    Fogagnolo, Marco
    Massi, Alessandro
    Pomelli, Christian Silvio
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 302 - 312
12345