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Organophosphorus Chemistry without PCl 3 : A Bridge from Hypophosphorous Acid to H‐Phosphonate Diesters
Author(s) -
Fisher Henry C.,
Prost Lucie,
Montchamp JeanLuc
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301412
Subject(s) - chemistry , phosphonate , alkyl , chlorine , nickel , chloride , organic chemistry , oxidative addition , chlorine atom , catalysis , polymer chemistry , medicinal chemistry , combinatorial chemistry
A process for the conversion of hypophosphorous acid (H 3 PO 2 , HPA) and alcohols into various H‐phosphonate diesters [(RO) 2 P(O)H] is described. The new reaction provides a missing bridge between HPA and important H‐phosphonates, completely avoiding the use of PCl 3 . Nickel chloride or nickel on silica catalyze the oxidative phosphorylation of alkyl phosphinates with various alcohols or water. The reaction is atom economic and avoids the formation of waste products. The previous need for both chlorine and base is completely avoided.