Mitsunobu Reaction Using Basic Amines as Pronucleophiles
Journal of Organic Chemistry
First page number:
Last page number:
A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system. © 2017 American Chemical Society.
Kang, J. Y.
Mitsunobu Reaction Using Basic Amines as Pronucleophiles.
Journal of Organic Chemistry, 82(13),