A Reagent-Controlled Phospha-Michael Addition Reaction of Nitroalkenes with Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas

Authors

Hai Huang, University of Nevada, Las VegasFollow
Jake Palmas, University of Nevada, Las Vegas
Jun Yong Kang, University of Nevada, Las VegasFollow

Document Type

Article

Publication Date

1-1-2016

Publication Title

Journal of Organic Chemistry

Volume

81

Issue

23

First page number:

11932

Last page number:

11939

Abstract

Bifunctional N-heterocyclic phosphine (NHP)-thioureas have been successfully applied for phospha-Michael addition reaction of nitroalkenes to afford diversely substituted β-nitrodiazaphosphonates. This transformation takes place at room temperature under catalyst-free conditions and exhibits broad functional group tolerance. The key to success in catalyst, additive-free reaction conditions is the suitable hydrogen-bond activation of the nitro group by a Brønsted acid (thiourea), which artfully combined with the highly nucleophilic NHP motif for a synergetic effect. Importantly, this transformation enables a two-step synthesis of pharmaceutically, biologically significant β-amino phosphonic acids. © 2016 American Chemical Society.

Language

English

Repository Citation

Huang, H., Palmas, J., Kang, J. Y. (2016). A Reagent-Controlled Phospha-Michael Addition Reaction of Nitroalkenes with Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas. Journal of Organic Chemistry, 81(23), 11932-11939.
http://dx.doi.org/10.1021/acs.joc.6b02490