Efficient and highly aldehyde selective Wacker oxidation.

نویسندگان

  • Peili Teo
  • Zachary K Wickens
  • Guangbin Dong
  • Robert H Grubbs
چکیده

A method for efficient and aldehyde-selective Wacker oxidation of aryl-substituted olefins using PdCl(2)(MeCN)(2), 1,4-benzoquinone, and t-BuOH in air is described. Up to a 96% yield of aldehyde can be obtained, and up to 99% selectivity can be achieved with styrene-related substrates.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.

The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceu...

متن کامل

Aldehyde-selective Wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst.

Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. (18) O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

متن کامل

Selective oxidation of primary alcohols to aldehydes with H5IO6/V2O5 in ionic liquid

An efficient protocol for the selective oxidation of primary alcohols to aldehydes withH5IO6/V2O5 in ionic liquid [bmpy][PF6] has been developed. High yields of the products, mildreaction conditions and simple experimental procedure make this protocol complementary tothe existing methods. The catalyst can be reused for several times without obvious loss of thecatalytic activity.

متن کامل

Mn (III) salen complex supported on graphene oxide nanosheets as a highly selective and recoverable catalyst for the oxidation of sulfides

In this study, Mn (III) salen complex was synthesized and immobilized onto the graphene oxide, which is modified by 3-chloropropyltrimethoxy silane. Heterogeneous catalyst was characterized by X-ray diffraction, transmission electron microscopy, thermogravimetric analysis, fourier transform infrared spectra, nitrogen adsorption−desorption isotherm and atomic absorption spectroscopy. The catalyt...

متن کامل

Fe3O4/FDU-12: A highly efficient and magnetically separable nano-catalyst for oxidation of alcohols

A series of Fe3O4 supported on mesoporous FDU-12 silica systems were prepared by the hydrothermal conditions. The surface properties of the functionalized catalyst were analyzed by a series of characterization techniques like FTIR, XRD, N2 adsorption–desorption and TEM. XRD and adsorption–desorption analysis shows that the mesostructure of FDU silica remains intact after Fe3O4 modifications, wh...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic letters

دوره 14 13  شماره 

صفحات  -

تاریخ انتشار 2012