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
  • [41] Nickel-catalyzed remote and proximal Wacker-type oxidation
    Binbin Liu
    Penghui Hu
    Fangning Xu
    Lu Cheng
    Mingxi Tan
    Wei Han
    Communications Chemistry, 2
  • [42] Dihydroxylation of olefins using air as the terminal oxidant
    Döbler, C
    Mehltretter, GM
    Sundermeier, U
    Beller, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) : 70 - 76
  • [43] CONVERSION OF METHYL KETONES INTO TERMINAL ACETYLENES AND (E)-TRISUBSTITUTED OLEFINS OF TERPENOID ORIGIN
    NEGISHI, EI
    KING, AO
    KLIMA, WL
    PATTERSON, W
    SILVEIRA, A
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12): : 2526 - 2528
  • [44] METAL CATALYSIS IN OXIDATION BY PEROXIDES .19. ON THE MECHANISM OF RHODIUM-CATALYZED OXIDATION OF TERMINAL OLEFINS TO METHYL KETONES BY DIOXYGEN
    BORTOLINI, O
    DIFURIA, F
    MODENA, G
    SERAGLIA, R
    JOURNAL OF MOLECULAR CATALYSIS, 1984, 22 (03): : 313 - 317
  • [45] Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid
    Donck, Simon
    Gravel, Edmond
    Shah, Nimesh
    Jawale, Dhanaji V.
    Doris, Eric
    Namboothiri, Irishi N. N.
    CHEMCATCHEM, 2015, 7 (15) : 2318 - 2322
  • [46] An alkene-NOx cell for the wacker-type oxidation of alkenes
    Otsuka, K
    Yamanaka, I
    Nishi, A
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2001, 148 (02) : D4 - D8
  • [47] Nickel-catalyzed remote and proximal Wacker-type oxidation
    Liu, Binbin
    Hu, Penghui
    Xu, Fangning
    Cheng, Lu
    Tan, Mingxi
    Han, Wei
    COMMUNICATIONS CHEMISTRY, 2019, 2 (1)
  • [48] DEACTIVATION EFFECTS IN THE SYNTHESIS OF METHYL ETHYL KETONE BY SELECTIVE OXIDATION OVER SOLID WACKER-TYPE CATALYSTS
    CENTI, G
    PERATHONER, S
    STELLA, G
    CATALYST DEACTIVATION 1994, 1994, 88 : 393 - 400
  • [49] RHODIUM(I) PROMOTED OXYGENATION OF TERMINAL OLEFINS TO METHYL KETONES BY MOLECULAR-OXYGEN
    DUDLEY, C
    READ, G
    TETRAHEDRON LETTERS, 1972, (52) : 5273 - &
  • [50] Development of PdCl2-DMA catalyst system for cocatalyst-free Wacker-type oxidation of various olefins
    Mitsudome, Takato
    Mizumoto, Keiichi
    Mizugaki, Tomoo
    Jitsukawa, Koichiro
    Kaneda, Kiyotomi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
12345