A practical protocol for the synthesis of ketones by Pd-catalyzed cross-coupling of phenol derivatives with nitroalkanes followed by a Nef-type reaction has been developed. The readily available nitroalkanes served as alkyl nucleophiles under basic conditions to couple with easy-to-handle phenol derivatives derived from naturally abundant phenols. The avoidance of using organometallics and organic halides makes this protocol more sustainable. The reaction was compatible with various functional groups, including nitro, cyano, acetyl, aldehyde, halide, and ester groups. Furthermore, the successful application of our method in drug synthesis exemplified its synthetic potential in pharmaceutical sciences. Preliminary mechanistic investigations strongly suggested the possible involvement of α-aryl-substituted nitroalkane intermediates.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.