Chemoselective Aerobic Oxidation of Alcohols Utilizing a Vanadium(V) Catalyst

被引:8
|
作者
Kitt, Maggie I. [1 ]
Amir, Emily [1 ]
Sloane, Eleanor R. [1 ]
Fraser, Douglas G. [1 ]
Cerritelli, John E. [1 ]
Sabanos, Caroline S. M. [1 ]
McNeely, James H. [1 ]
Snyder, John K. [1 ]
Doerrer, Linda H. [1 ]
Beeler, Aaron B. [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
基金
美国国家科学基金会;
关键词
vanadium catalysis; chemoselective oxidations; aerobic oxidation; diols; ALPHA-HYDROXY ESTERS; SECONDARY ALCOHOLS; PROPARGYLIC ALCOHOLS; ALDEHYDES; EFFICIENT; MECHANISM; OXYGEN; DECOMPOSITION; COMPLEXES; MODELS;
D O I
10.1021/acscatal.3c05638
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Work remains to develop an aerobic catalyst that will selectively oxidize secondary alcohols in the presence of primary alcohols. In principle, this is possible when there is an oxidation potential preference for doing so. One potential strategy is the use of a low oxidation potential catalyst. Recently, we reported a dimeric vanadium(V)-(mu-O)(2) perfluoropinacolate (pin(F)) complex with the ability to oxidize alcohols via dehydrogenation that was sensitive to the alcohol redox potential. Herein, we report the scope, chemoselectivity, and insights into the mechanism by which V(V) cat performs oxidations on activated primary and secondary alcohols.
引用
收藏
页码:4799 / 4806
页数:8
相关论文
共 50 条
  • [41] AEROBIC OXIDATION OF ALCOHOLS WITH RUTHENIUM-COBALT BIMETALLIC CATALYST IN THE PRESENCE OF ALDEHYDES
    MURAHASHI, SI
    NAOTA, T
    HIRAI, N
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26): : 7318 - 7319
  • [42] Supported Cobalt Oxide Nanoparticles As Catalyst for Aerobic Oxidation of Alcohols in Liquid Phase
    Zhu, Junjiang
    Kailasam, Kamalakannan
    Fischer, Anna
    Thomas, Arne
    ACS CATALYSIS, 2011, 1 (04): : 342 - 347
  • [43] Aerobic oxidation of primary alcohols by a new mononuclear CuII-radical catalyst
    Chaudhuri, P
    Hess, M
    Weyhermüller, T
    Wieghardt, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (08) : 1095 - 1098
  • [44] NOVEL AND SELECTIVE METHOD FOR THE AEROBIC OXIDATION OF BENZYLIC ALCOHOLS IN THE ABSENCE OF METAL CATALYST
    Shi, Shenyi
    Kong, Aiguo
    Zhao, Xinhua
    Shan, Yongkui
    SYNTHETIC COMMUNICATIONS, 2011, 41 (20) : 3066 - 3070
  • [45] Bimetallic synergistic Au/CuO-hydroxyapatite catalyst for aerobic oxidation of alcohols
    Tian, Tao
    Liu, Ying
    Zhang, Xungao
    CHINESE JOURNAL OF CATALYSIS, 2015, 36 (08) : 1358 - 1364
  • [46] Mild Aerobic Oxidation of Secondary Alcohols with Water Tolerant Cu(I) Catalyst
    Heshmatnia, Faranak
    Zupanc, Anze
    Eronen, Aleksi
    Lagerspets, Emi
    Install, Joseph
    Repo, Timo
    CHEMSUSCHEM, 2024,
  • [47] New highly active copper(I) catalyst for aerobic oxidation of primary alcohols
    Lagerspets, Emi
    Lagerblom, Kalle
    Heliovaara, Eeva
    Hiltunen, Otto-Matti
    Moslova, Karina
    Nieger, Martin
    Repo, Timo
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [48] Chemoselective deprotection/oxidation of protected alcohols with Magtrieve™
    Park, ST
    Ko, KY
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (03) : 367 - 368
  • [49] CHEMOSELECTIVE OXIDATION OF BENZYLIC ALCOHOLS BY FREMY SALT
    MOREY, J
    DZIELENZIAK, A
    SAA, JM
    CHEMISTRY LETTERS, 1985, (03) : 263 - 264
  • [50] Effective cleavage of ditertiary glycols via vanadium(V)-catalyzed aerobic oxidation
    Kirihara, Masayuki
    Yoshida, Katsumi
    Noguchi, Takuya
    Naito, Sayuri
    Matsumoto, Nobuchika
    Ema, Yukinori
    Torii, Motoya
    Ishizuka, Yuki
    Souta, Ikuo
    TETRAHEDRON LETTERS, 2010, 51 (28) : 3619 - 3622