Facile access to nitroalkanes: Nitration of alkanes by selective C[sbnd]H nitration using metal nitrate, catalyzed by in-situ generated metal oxide

Article abstract of DOI:10.1016/j.catcom.2020.106035

Direct C ? H functionalization of inactive alkanes is an important strategy to streamline the preparation of functional molecules. Herein, we describe an operationally simple and effective alkane C ? H nitration reaction to access versatile nitroalkanes without cleavage of the C ? C skeleton. Nontoxic and inexpensive metal nitrate (Fe(NO₃)₃·9H₂O) plays a dual role as catalyst precursors as well as nitro sources for the transformation. Experimental evidence and theoretical modeling have shown the formation of iron oxide as a key catalytic species for the alkane C ? H and NO₂ activation, which favors a stepwise radical mechanism with initial alkyl radical formation.