Efficient and Highly Aldehyde Selective Wacker Oxidation
نویسندگان
چکیده
منابع مشابه
Efficient and highly aldehyde selective Wacker oxidation.
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.
متن کاملCatalytic Anti-Markovnikov Transformations of Hindered Terminal Alkenes Enabled by Aldehyde-Selective Wacker-Type Oxidation.
A new strategy for the functionalization of sterically hindered terminal olefins is reported. Alkenes bearing quaternary carbons at the allylic or homoallylic position are readily oxidized to the corresponding aldehydes by palladium/copper/nitrite catalysis. A broad range of functional groups including esters, nitriles, silyl ethers, vinylogous esters, ketones, lactones, and β-ketoesters are to...
متن کاملAldehyde-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 کاملUnraveling the Wacker oxidation mechanisms.
The Wacker processsolefin oxidation via a Pd(II)Cl2 catalyst and an air-recyclable CuCl2 co-oxidant (Scheme 1)swas one of the most important industrial breakthroughs in the fabrication of organic chemicals, and is widely regarded as one of the quintessential organometallic processes.1 Besides its industrial importance, the Wacker process and its analogues are continually used in fields relating...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2012
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol301240g