Baeyer-Villiger oxidation review

The Baeyer-Villiger oxidation of ketones represents a powerful synthetic method that breaks carbon-carbon bonds in an oxygen insertion process to deliver lactones. A recent comprehensive review by ten Brink et describes the different... 

Nevertheless, Celia et al. have proved that employing MCPBA as secondary oxidant in TEMPO-mediated oxidations may have a number of advantages when a one-pot oxidation of an alcohol with a concurrent alkene epoxidation or a Baeyer-Villiger oxidation is desired.6 The use of MCPBA as a secondary oxidant in TEMPO-mediated alcohol oxidations was recently reviewed.7... 

The recent development of inorganic crystalline-supported metal catalysts for various liquid-phase oxidation reactions such as alcohol oxidation, epoxidation, Baeyer-Villiger oxidation and oxidation via C—H activation using molecular oxygen (02) or hydrogen peroxide (H202) as an oxidant are reviewed in this chapter. 

A brief review of procedures for asymmetric metal-catalyzed Baeyer-Villiger oxidations is given with asymmetric copper-catalyzed synthesis of 3-phenyl-2-oxepanone as representative of the enantioselective synthesis of lactones from cyclic ketones . 

Asymmetric epoxidations of alkenes catalysed by chiral monomeric organorhenium (VII) and organomolybdenum(VI) compounds,160 ketones,161 and salen-metal complexes162 have been reviewed. The advances in the catalysed Baeyer-Villiger oxidation... 

Under the name Oxone an oxidation agent has been introduced, consisting of KHSO4-K2SO4-2KHSO5. Solid Oxone converts methylenic functions under anhydrous, biphasic conditions to carbonyl compounds under the catalytic influence of ligand-modified Mn porphyrins and phase-transfer catalysts (e. g., acetophenone is obtained from ethylbenzene). In the case of cyelohexane, e-caprolactone results as well as cyclohexanol and -one ([219 b, 241] cf. also Baeyer-Villiger oxidation). Biphasic oxidations with methyltrioxorhenium (e. g., to epoxides) are reviewed in Section 3.3.13 [244 i]. 

Hexoses - The synthesis of hexoseptanose derivatives by ring expansion of uloses, Baeyer Villiger oxidation of inositols, or Baeyer-Fischer reaction of sugar dialdehydes has been reviewed. ... 

Other interesting articles and reviews include polyvinyl alcohol composites, generally [62], with proteins [63-65], starch [66], chitosan [67], simple sugars [68], and a Baeyer Villiger oxidation [95] (Scheme 3) of a an ethylene-vinyl alcohol copolymer to produce a biodegradable polyhydroxypolyester. 

For a review of the hydrogen peroxide-mediated Baeyer-Villiger oxidation, and leading references, see Uyanik, M. Ishihara, K. ACS Catal. 2013, 3, 513-520. 

Oxidation of carbonyl compounds is an important area of oxidation and involves a variety of different reaction types. This area has been reviewed by Bolm in Chapter 9 of the book Modem Oxidation Methods (2004), and the present chapter is an update of this review. We have focused on two areas of carbonyl oxidation where important developments have occurred (i) oxidation of aldehydes to carboxylic adds and (ii) Baeyer-Villiger oxidation. 

Preparing Aldehydes and Ketones A Review Introduction to Nucleophilic Addition Reactions Oxygen Nucleophiles Nitrogen Nucleophiles Mechanism Strategies Sulfur Nucleophiles Hydrogen Nucleophiles Carbon Nucleophiles Baeyer-Villiger Oxidation of Aldehydes and Ketones Synthesis Strategies... 

The Baeyer-Wliger oxidation of cyclic ketones provides general access to six- and seven-membered lactones. However, due to relatively less availability of cyclobutanones, y-lactone synthesis through the Baeyer-Villiger oxidation is not so common process. Recent achievements in this oxidation are reviewed in a paper by Ishihara and Uyanik [17]. 

The Baeyer-Villiger oxidation of 7-oxabicyclo[2.2.1]heptan-2-ones is the most used reaction to cleave a C-C bond of the 7-oxabicyclo[2.2.1]heptanes. Other routes have used retro-Claisen, retro-Diekmann, and Grob fragmentations. They have been reviewed elsewhere [11]. Enoxysilanes derived from 7-oxanorboman-2-ones can be ozonolyzed into 2,5-anhydrouronic acid derivatives, precursors for C-nucleosides [225]. 

A review of oxidation reactions in imidazolium ionic liquids has addressed oxidations of alcohols, aromatics, alkanes, and sulfur-containing compounds and the Baeyer-Villiger and Corey-Chaykovsky methods. ... 

For selected reviews on the Baeyer-Villiger (BV) oxidation (a) ten Brink, G.-J., Arends, I. W. C. E., Sheldon, R. A. (2004). The Baeyer-Villiger reaction new developments toward greener procedures. Chemical Reviews, 104, 4105-4123. For selected reviews on asymmetric BV oxidation (b) Bohn, C., Beckmann, O. (1999). Baeyer-Villiger reaction. In Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Comprehensive Asymmetric Catalysis. Springer, Berlin, Vol. 2, pp. 803-812. 

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