Overview on the phosphonation of the C=X functional groups utilizing alkyl phosphites

• Published in: Synthetic communications Vol. 47; no. 18; pp. 1631 - 1660
• Main Authors: Ganoub, Neven A., Sabry, Eman, Abdou, Wafaa M.
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis 17.09.2017; Taylor & Francis Ltd
• Subjects: 3-CR, three component reaction; Aldehydes; Alkenes; Alkyl phosphites; aminophosphonates; aminopropylated silica gel; and; APSiO; Chemists; DAPs, dialkyl phosphites; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DEP, diethyl phosphite; DMP, dimethyl phosphite; Esters; Functional groups; Hydrazones; hydroxyphosphonates; Imines; Inorganic salts; Isocyanates; Ketones; LB, Lewis base; magnesium perchlorate; MCR, multiple component reactions; MCRs, pyridinium hydrohalides; Mg(ClO; N-OPCs, nitrogen-organophosphorus compounds; OPCs, organophosphorus compounds; Oximes; peptidomimics; phosphorylation; PyH; Reagents; SiBr, trimethylsilyl bromide; TAPs, trialkyl phosphites; TBD, 1,5,7-triazabicyclo[4.4.0]dec-5-ene; TMP, trimethyl phosphite; TMSCl, chlorotrimethylsilane
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2017.1346811

The main objective of this survey is to provide a comprehensive review of recent achievements related to the phosphonation processes, applying alkyl phosphites and different electrophiles (C˭X, X: O, N, or C). The review discusses the important reactions of trialkyl and dialkyl phosphite reagents with a variety of aldehydes, ketones, aldimines, ketimines, hydrazones, oximes, diazo compounds, thio- and isocyanates as well as activated olefins as a convenient methodology for the synthesis of biologically important α -hydroxy- and α -aminophosphonates as well as heterocycles containing phosphorus and substituted heterocyclic phosphor esters. We are herein concentrating only on reactions that lead to phosphorylated products as they represent a vast and important research area of interest for academic, as well as for industrial, pharmaceutical and phytopharmaceutical chemists. The literature survey has been fully covered up by our group and others over the last 25 years.