Palladium(II)-mediated oxidation of alcohols using 1,2-dichloroethane as Pd(O) reoxidant

Aı̈t-Mohand, Samia; Hénin, Françoise; Мuzart, Jacques

doi:10.1016/0040-4039(95)00286-3

Cited by 72 publications

(22 citation statements)

References 26 publications

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“…[30,31] In the course of studying allylic alkylation reactions, Echavarren and co-workers discovered that [Pd(dba) 2 ](10 %)/PPh 3 (30 %) catalyzes the oxidation of allylic alcohols in toluene under an air atmosphere. Modest yields were generally obtained (38-56 %, 90 % for cinnamyl alcohol).…”

Section: Early Developmentsmentioning

confidence: 99%

“…Modest yields were generally obtained (38-56 %, 90 % for cinnamyl alcohol). [30] Later, Muzart and co-workers reported the PdCl 2 -catalyzed oxidation of indanol (51 % yield) in refluxing hexane under an air atmosphere [31] with the phase-transfer catalyst andogen 464 (10 %) and Na 2 CO 3 (2 equiv).…”

Section: Early Developmentsmentioning

confidence: 99%

“…(31)], deprotonation of the carboxylic acid additive led to a switch in the product stereochemistry from cis to trans. TBS rather than a TMS protecting group hinders the formation of the dehydrosilylation by-product that arises from from b-hydride elimination (Scheme 12).…”

Section: Intramolecular Oxidation Of Alkenes: Oxidative Hetero-and Camentioning

confidence: 99%

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Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen‐Coupled Turnover

2004

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Selective aerobic oxidation of organic molecules is a fundamental and practical challenge in modern chemistry. Effective solutions to this problem must overcome the intrinsic reactivity and selectivity challenges posed by the chemistry of molecular oxygen, and they must find application in diverse classes of oxidation reactions. Palladium oxidase catalysis combines the versatility of Pd(II)-mediated oxidation of organic substrates with dioxygen-coupled oxidation of the reduced palladium catalyst to enable a broad range of selective aerobic oxidation reactions. Recent developments revealed that cocatalysts (e.g. Cu(II), polyoxometalates, and benzoquinone) are not essential for efficient oxidation of Pd(0) by molecular oxygen. Oxidatively stable ligands play an important role in these reactions by minimizing catalyst decomposition, promoting the direct reaction between palladium and dioxygen, modulating organic substrate reactivity and permitting asymmetric catalysis.

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Section: Early Developmentsmentioning

confidence: 99%

Section: Early Developmentsmentioning

confidence: 99%

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Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen‐Coupled Turnover

2004

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“…Similarly, PdCl 2 , in combination with sodium carbonate and a tetraalkylammonium salt, Adogen 464, as a phase transfer catalyst, catalyzed the aerobic oxidation of alcohols; for example, 1,4-and 1,5-diols afforded the corresponding lactones (Eq. (5.11)) [72,73].…”

Section: Substratementioning

confidence: 99%

Modern Oxidation of Alcohols Using Environmentally Benign Oxidants

Arends

Sheldon

2010

Modern Oxidation Methods

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“…Similarly, PdCl 2 , in combination with sodium carbonate and a tetraalkylammonium salt, Adogen 464, as a phase transfer catalyst, catalyzed the aerobic oxidation of alcohols, e. g., 1,4-and 1,5-diols afforded the corresponding lactones [Eq. (14)] [78,79].…”

mentioning

confidence: 99%