General Route for Preparing β‑Nitrocarbonyl Compounds Using Copper Thermal

ABSTRACT: Using a simple copper catalyst, the alkylation of nitroalkanes with α-bromocarbonyls is now possible. This method provides a general, functional group tolerant route to β-nitrocarbonyl compounds, including nitro amides, esters, ketones, and aldehydes. The highly sterically dense, functional group rich products from these reactions can be readily elaborated into a range of complex nitrogen-containing molecules, including highly substituted β-amino acids. Nitroalkanes are extraordinarily useful intermediates inorganic synthesis.1 These compounds participate in a wide range of carbon−carbon bond-forming reactions (including Henry reactions,2 conjugate additions,2 allylations,3 and arylations4), serve as starting materials for the installation of numerous functional groups (including alkylamines, ketones, hydroxyl amines, alkanes),2 and serve as radical precursors (Scheme 1).5 Among nitroalkanes, nitrocarbonyl compounds are a partic