N-P Bond Formation
Phosphorylation of amines, alcohols, and sulfoximines provides various phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates using molecular iodine as a catalyst and H2O2 as the sole oxidant under mild reaction conditions.
J. Dhineshkumar, K. R. Prabhu, Org. Lett., 2013, 15, 6062-6065.
A diaryldiselenide catalyzes a cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.
Handoko, Z. Benslimane, P. S. Arora, Org. Lett., 2020, 22, 5806-5810.
Simply heating secondary phosphine oxides and O-benzoylhydroxylamines in the presence of K2CO3 gives phosphinic amides in moderate to excellent yields under air. This method provides a practical and catalyst-free method for the synthesis of various synthetically valuable phosphinic amides.
R. Zhu, C. Pan, Z. Gu, Org. Lett., 2015, 17, 5862-5865.
Reductive radical cyclization of N-allyl-N-dimethylphosphinoyl-2-aminopropyl phenyl selenide using tris(trimethylsilyl)silane (TTMSS) / AIBN under UV irradiation gave the corresponding pyrrolidine in 74% yield and a cis/trans ratio of 10/1 which was superior to thermal cyclization.
D. Shanks, S. Berlin, M. Besev, H. Ottosson, L. Engman, J. Org. Chem., 2004, 69, 1487-1491.