In this work, a new catalytic approach for the C-O activation of enol phosphates based on a palladium supported on layered double hydroxide was developed. In this case, two different ketene aminal phosphates were used as models to study the synthesis of -phenyl enecarbamates N-Boc/CBz under the Suzuki-Miyaura conditions. The use of an ortho-bromoaniline as precursor allowed the synthesis of the 2-phenyl indole through an arylation/Heck cyclization. Catalyst reusability enabled the synthesis of the heterocycle in moderate yields for four consecutive runs.
The recovery of waste materials with potential for synthetic transformations is a major field in science. However, just few experiments have been devoted to undergraduate students by exploring some consistent subjects in light of simple, natural resources. Nucleophilicity is a central subject in chemistry and there are significant synthetic models to exploit it in contrast to basicity. Here we present a laboratory experiment that utilizes hands-on research to be implemented in an organic chemistry lab by using benzyl isothiocyanate (BITC) from papaya seeds as raw material for the preparation of thioureas in a fast and visually indicative experiment. Subjects such as green chemistry, extraction methods, nucleophilicity, chromatography and NMR spectroscopy can be emphasized in order to implement a project-based approach. This experiment shows flexibility concerning the procedures and the use of biomass raw materials towards the reinforcement of a research-like experience and critical-thinking skills.
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