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Oxidative cleavage vs wacker-type profiles in oxygenation reactions

AutorAbril, Paula ; Río, M. Pilar del ; López, José A. ; Ciriano, Miguel A. ; Tejel, Cristina
Fecha de publicación2014
CitaciónXXXII GEQO (2014)
Resumen[Work hypothesis and objective]: The catalytic oxidation of olefins to give oxygenated compounds such as aldehydes, ketones or ethers are some of the most important transformations in the industry due to the high impact that these products have in our daily life. Despite the enormous efforts of the chemists, some of these processes are still dangerous or contaminant. For example, ozonolysis is a good method for the synthesis of aldehydes; however ozone can be explosive under the drastic reaction conditions used. Other oxidizing agents such as permanganates, iodates or dichromates are toxic. Therefore, the search of alternative systems able to cleanly and safetly oxidize C=C bonds is a priority goal in current chemistry. In this sense, the use of oxygen from the air as a friendly oxidant in the oxygenation of organic compounds is a challenge that remains unsolved nowadays. [Results]: In this communication we will show that rhodium complexes bearing robust bidentate N,O-ligands are able to activate oxygen and transfer it to olefins to give a variety of oxygenated species Thus, ketones, ethers or aldehydes can be isolated from a fine tuning of the reaction conditions. Mechanistic features directing the selectivity to one or other type of products will be discussed. In addition, one complex derived from the regioselective hydroxylation of one of the C=C bonds of cod (1,5- cyclooctadiene) has also been isolated and its formation will be discussed in the overall scheme.
DescripciónTrabajo presentado a la XXXII Conference Expert Group Meeting on Organometallic Chemistry celebrada en Tarragona (España) del 17 al 19 de septiembre de 2014.
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