Catalytic, PMe3-mediated conversion of secondary nitroalkanes to ketones: a very mild Nef-type process

Aliphatic secondary nitro compounds are converted to ketones at room temperature, usually in 90-100% yields, by a one-pot reaction with 220-250 mol % of trimethylphosphine (PMe3) and 50-100 mol % of tBuC6H4SSC6H4tBu or PhthN-SePh, or 20 mol % of both additives. Thus, very mild catalytic variants of the reductive Nef-like reactions are disclosed.

Graphical abstractBy addition of 50-100 mol % of tBuC6H4SSC6H4tBu or PhthN-SePh, or of only 20 mol % of both additives, to secondary nitro compounds into a 1.0 M THF solution of PMe3, nitro groups are readily reduced to imino groups, at room temperature.Download full-size image