Mitsunobu Reaction Using Basic Amines as Pronucleophiles

Authors

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

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.

File Format

pdf

File Size

1169 kb

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