Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing
small molecules in medicine
necessitates the continued search for improved methods for C–N
bond formation. Electrophilic amination often requires a disparate
toolkit of reagents whose selection depends on the specific structure
and functionality of the substrate to be aminated. Further, many of
these reagents are challenging to handle, engage in undesired side
reactions, and function only within a narrow scope. Here we report
the use of diazirines as practical reagents for the decarboxylative
amination of simple and complex redox-active esters. The diaziridines
thus produced are readily diversifiable to amines, hydrazines, and
nitrogen-containing heterocycles in one step. The reaction has also
been applied in fluorous phase synthesis with a perfluorinated diazirine.