Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Mitsunobu Reaction Using Basic Amines as Pronucleophiles

Mitsunobu Reaction Using Basic Amines as Pronucleophiles
Hai Huang, Jun Yong Kang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00622

DOI: 10.1021/acs.joc.7b00622

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