Substituted amines are important compounds that are present in many products such as amino acids, nucleotides and alkaloids. They play an important role in chemistry and biology, being used as versatile building blocks for organic and biological systems, agrochemicals and pharmaceuticals. Given the significance of these compounds, developing straightforward and economic synthetic methods has become an important research topic, in both, laboratory synthesis and the chemical industry. Despite its importance and prevalence, there are several disadvantages associated with the conventional process such as non-catalytic reactions using hazardous alkyl halides for substitutions, handling of unstable aldehydes, which in some cases are not available or undergo unwanted side-reactions like aldol condensations, and the control for mono alkylated products. Compared with traditional methods, catalytic method for reductive alkylation of amines using carboxylic acids has become an attractive route because of the step economy and easy availability of the carboxylic acids. Despite of the progress done in this field, there is a lack of versatility, functional group tolerance, employing hard reaction conditions and long reaction times. In our research group, being aware of the importance of the development of environmental friendly routes with perfect atom economy, in which minimize the formation of by-products and the number of steps, we disclose a catalyst method with Mo(CO)6 for straightforward N-alkylation of amines using available carboxylic acids in the presence of a silane as reducing agent, with high level of selectivity, good functional group tolerance and good to high yields. Moreover, with our green methodology, we can selectively form amines and enamines depending of the carboxylic acid employed under mild reaction conditions and in short reaction times. Furthermore, enamines are efficiently functionalized into α-amino nitriles under one pot protocol

Chemoselective reductive N-alkylation of amines with carboxylic acids under hydrosilylation conditions and direct functionalization

2019 Fall National Meeting

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