Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones

被引：53
|
作者：
Chaudhari, Dipali A. [1 ]
Fernandes, Rodney A. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 05期
关键词：
SUPERCRITICAL CARBON-DIOXIDE; DESS-MARTIN PERIODINANE; PALLADIUM-CATALYZED OXIDATION; PROTECTED ALLYLIC AMINES; SELECTIVE OXIDATION; AEROBIC OXIDATION; SECONDARY ALCOHOLS; MOLECULAR-OXYGEN; SOLE OXIDANT; EFFICIENT;
D O I：
10.1021/acs.joc.6b00137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.
引用
收藏
页码：2113 / 2121
页数：9
相关论文
共 50 条
  • [21] Phenanthroline Decorated by a Crown Ether as a Module for Metallorganic-Polyoxometalate Hybrid Catalysts: The Wacker Type Oxidation of Alkenes with Nitrous Oxide as Terminal Oxidant
    Ettedgui, Jessica
    Neumann, Ronny
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) : 4 - +
  • [22] Highly selective Wacker oxidation of terminal olefins using magnetically recyclable Pd-Fe3O4 heterodimer nanocrystals
    Byun, Sangmoon
    Chung, Jooyoung
    Jang, Youngjin
    Kwon, Jungmin
    Hyeon, Taeghwan
    Kim, B. Moon
    RSC ADVANCES, 2013, 3 (37): : 16296 - 16299
  • [23] Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
    Wickens, Zachary K.
    Skakuj, Kacper
    Morandi, Bill
    Grubbs, Robert H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) : 890 - 893
  • [24] Aldehydes from Pd-catalysed oxidation of terminal olefins
    Muzart, Jacques
    TETRAHEDRON, 2007, 63 (32) : 7505 - 7521
  • [25] Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules
    Liu, Binbin
    Jin, Fengli
    Wang, Tianjiao
    Yuan, Xiaorong
    Han, Wei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) : 12712 - 12717
  • [26] Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst
    Wickens, Zachary K.
    Morandi, Bill
    Grubbs, Robert H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) : 11257 - 11260
  • [27] Catalyst-Controlled Wacker-Type Oxidation of Protected Allylic Amines
    Michel, Brian W.
    McCombs, Jessica R.
    Winkler, Andrea
    Sigman, Matthew S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7312 - 7315
  • [28] Anti-Markovnikov oxidation and hydration of terminal olefins
    Guo, Jiayi
    Teo, Peili
    DALTON TRANSACTIONS, 2014, 43 (19) : 6952 - 6964
  • [29] Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents
    Wu, Shuang
    Li, Junzhao
    He, Ru
    Jia, Kunfang
    Chen, Yiyun
    ORGANIC LETTERS, 2021, 23 (23) : 9204 - 9209
  • [30] Copper-Catalyzed Oxidative -Ketoacylations of Sulfoximines with Aryl Methyl Ketones and Dioxygen as Terminal Oxidant
    Cheng, Hanchao
    Bolm, Carsten
    SYNLETT, 2016, 27 (05) : 769 - 772
12345