Using a commercially available, inexpensive,
and abundant copper
catalyst system, an efficient α-functionalization of nitroalkanes
with propargyl bromides is now established. This mild and robust method
is highly functional group tolerant and provides straightforward access
to complex secondary and tertiary homopropargylic nitroalkanes. Moreover,
the utility of these α-propargylated nitroalkanes is demonstrated
through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.
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