Mitsunobu Reaction Using Basic Amines as Pronucleophiles

Authors

H Huang, University of Nevada, Las VegasFollow
J Y. Kang, University of Nevada, Las VegasFollow

Document Type

Article

Publication Date

1-1-2017

Publication Title

Journal of Organic Chemistry

Volume

82

Issue

13

First page number:

6604

Last page number:

6614

Abstract

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.

Language

english

Repository Citation

Huang, H., Kang, J. Y. (2017). Mitsunobu Reaction Using Basic Amines as Pronucleophiles. Journal of Organic Chemistry, 82(13), 6604-6614.
http://dx.doi.org/10.1021/acs.joc.7b00622