Selective Aerobic Oxidation of Allylic Alcohols to Carbonyl Compounds Using Catalytic Pd(OAc)<sub>2</sub>: High Intramolecular Selectivity.

Batt, Frédéric; Bourcet, Emmanuel; Kassab, Youssef; Fache, Fabienne

doi:10.1002/chin.200748031

Cited by 2 publications

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“…In 2002, Sigman reported a triethylamine-ligated Pd II catalyst system for aerobic oxidation of benzylic, allylic, and aliphatic alcohols at room temperature (Scheme ). − This system provided milder conditions for substrate oxidation than previously reported palladium catalysts, such as Uemura’s Pd(OAc) 2 /py system, which required elevated temperature (80 °C) for efficient reactivity (cf. section ).…”

Section: Monodentate Ligandsmentioning

confidence: 99%

Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

et al. 2017

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Palladium-catalyzed aerobic oxidation reactions have been the focus of industrial application and extensive research efforts for nearly 60 years. A significant transition occurred in this field approximately 20 years ago, with the introduction of catalysts supported by ancillary ligands. The ligands play crucial roles in the reactions, including promotion of direct oxidation of palladium(0) by O, bypassing the typical requirement for Cu salts or related redox cocatalysts to facilitate oxidation of the reduced Pd catalyst; facilitation of key bond-breaking and bond-forming steps during substrate oxidation; and modulation of chemo-, regio-, or stereoselectivity of a reaction. The use of ligands has contributed to significant expansion of the scope of accessible aerobic oxidation reactions. Increased understanding of the role of ancillary ligands should promote the development of new synthetic transformations, enable improved control over the reaction selectivity, and improve catalyst activity and stability. This review surveys the different ligands that have been used to support palladium-catalyzed aerobic oxidation reactions and, where possible, describes mechanistic insights into the role played by the ancillary ligand.

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Section: Monodentate Ligandsmentioning

confidence: 99%

Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

et al. 2017

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“…α- Bulnesone was synthesized by oxidation of 6b using palladium-catalyzed oxidation with molecular oxygen . To a stirred solution of 6b (660 mg, 3 mmol) in THF/toluene (15%, 30 mL) was added Pd(OAc) 2 (20.2 mg, 90 μmol) and Et 3 N (20 μL, 0.14 mmol).…”

Section: Materials and Methodsmentioning

confidence: 99%

Comparison of the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions

Huang

Sefton

Taylor

2015

J. Agric. Food Chem.

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Deuterium-labeled guaiane derivatives and their precursors, namely, d5-2R-rotundol (11a), d5-2S-rotundol (11b), d5-bulnesone (14), d5-2R-bulnesol (16), d7-α-guaiene (10), and d7-α-bulnesene (15), were synthesized in good yields as GC-MS internal standards for comparing the behavior of α-guaiene (1) and α-bulnesene (5) under autoxidative conditions. It was found that approximately 99% of α-guaiene coated onto filter paper and exposed to air at ambient temperature was autoxidized after 48 h and up to 7% of rotundone (3) and 0.6% of rotundols (2a/b) were formed during this period. Autoxidation of α-bulnesene (5) was considerably slower, with approximately 80% remaining after 2 days and yielding less than 1.5% of α-bulnesone (7) and 0.3% and 0.9% of bulnesols 6a and 6b, respectively, after 5 days. The results indicate the feasibility of rapid changes of aroma profiles of herbs and other plant materials over time when exposed to air.

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Selective Aerobic Oxidation of Allylic Alcohols to Carbonyl Compounds Using Catalytic Pd(OAc)₂: High Intramolecular Selectivity.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 2 publications

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Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

Comparison of the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions

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Selective Aerobic Oxidation of Allylic Alcohols to Carbonyl Compounds Using Catalytic Pd(OAc)2: High Intramolecular Selectivity.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 2 publications

References 0 publications

Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

Comparison of the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions

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About

Selective Aerobic Oxidation of Allylic Alcohols to Carbonyl Compounds Using Catalytic Pd(OAc)₂: High Intramolecular Selectivity.