Abstract
We report a Cu-catalysed oxidative coupling of aliphatic amines with benzylic and aliphatic boronic esters to give high value alkyl amines, products found widely in applications from medicinal chemistry to materials science. This operationally simple reaction, which can be performed on gram scale, runs under mild conditions and exhibits broad functional group tolerance. The terminal oxidant of the reaction is O2 from the air, avoiding the need for additional chemical oxidants. Investigation into the reaction mechanism suggests that the boronic ester is activated by an aminyl radical, formed through oxidation of the amine by the Cu catalyst, to give a key alkyl radical intermediate. To demonstrate its utility and potential for late-stage functionalization, we showcase the method as the final step in the total synthesis of a TRPV1 antagonist.
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This file contains experimental methods, characterisation data, and copies of NMR spectra associated with the article.
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Video To Demonstrate Methodology
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This video has been created to demonstrate how we carry out our method for the Cu-catalysed amination of alkylboronic esters with aliphatic amines. This includes some background to the area of chemical research, a detailed view of how we set up and perform our reactions, and some problem solving tips.
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