title: A Reagent-Controlled Phospha-Michael Addition Reaction of Nitroalkenes with Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Nevada Las Vegas , 4505 S. Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.|Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University , No. 30 Puzhu Road (S), Nanjing 211816, People's Republic of China.
authors.forename: Hai
authors.initials: H
authors.lastname: Huang
authors.affiliation: Department of Chemistry and Biochemistry, University of Nevada Las Vegas , 4505 S. Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.
authors.forename: Jake
authors.initials: J
authors.lastname: Palmas
authors.affiliation: Department of Chemistry and Biochemistry, University of Nevada Las Vegas , 4505 S. Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.
authors.forename: Jun Yong
authors.initials: JY
authors.lastname: Kang