Reações de alilação e crotilação de diferentes aldeídos por trifluoroboratos orgânicos catalisada por aril-amidoximas

Abstract

First they were synthesized eight different aryl-amidoximes with moderate to excellent yields (35-91%). In parallel, the potassium allyltrifluoroborate and cis-crotyltrifluoroborate were synthesized also in good yields (78-75%). Properly synthesized and characterized the aryl-amidoximes and organic trifluoroborates, broke for studies of reaction conditions for the allylation of aldehydes. First, a study was made of the amount of benzamidoxime after a study of the best solvents proportion of water:dichloromethane. Established the lowest amount of the amidoxime and the best solvent system, broke to study the allylation reaction using different catalyst aryl-amidoximes. It was found that the p-bromobenzamidoxime showed the best result and the same was used in the continuation of studies. Established two reaction parameters (the aryl-amidoxime better and solvent system), left to the allylation reaction seventeen different aldehydes in which were found satisfactory results for the new method employed obtaining as a final product the homoallylic alcohols with moderate income excellent (40-93%). It was also carried out a study of chemoselectivity of the method, which has been verified the effectiveness of the method for obtaining the products of interest with good to excellent yields (75-93%). After these studies went up to the use of potassium cis-crotyltrifluoroborate under the same reaction conditions established in previous studies and also found themselves the effectiveness of the method for obtaining the products of interest with proceeds considered good to excellent (84-95% ).