Catalytic and Direct Oxyphosphorylation of Alkenes with Dioxygen and H‐Phosphonates Leading to β‐Ketophosphonates

Abstract

Direct access: The title reaction has been developed under mild reaction conditions (see scheme; DMSO=dimethyl sulfoxide). This reaction can be effectively scaled up and offers not only a green and attractive approach to β‐ketophosphonates, but also a useful example of direct incorporation of an oxygen atom from dioxygen into organic frameworks.

Cu/Fe‐Cocatalyzed Formation of β‐Ketophosphonates by a Domino Knoevenagel–Decarboxylation–Oxyphosphorylation Sequence from Aromatic Aldehydes and H‐Phosphonates

“…In such processes, multiple carbon–carbon or carbon–heteroatom bonds are formed concomitantly, extensive exploration of which, as one of the ultimate goals of synthetic organic chemistry, fascinates and appeals to organic chemists 3. As simple and readily available starting substrates, benzaldehydes have been employed in some elegant domino sequence reactions,4,10 yet very few have involved domino decarboxylation reactions 4a…”

Silver‐Catalyzed Oxidative C(sp3)−P Bond Formation through C−C and P−H Bond Cleavage

“…[4] However,tothe best of our knowledge,noexample of silvercatalyzed carbon-heteroatom bond formation through C À C bond activation has been described. This reaction provided facile access to aseries of heavily functionalized b-ketophosphonates, [6] which are omnipresent in awide range of biologically active molecules,n atural products,a nd functional materials.Compounds of this type are also widely employed as synthetic intermediates and metal ligands. This reaction provided facile access to aseries of heavily functionalized b-ketophosphonates, [6] which are omnipresent in awide range of biologically active molecules,n atural products,a nd functional materials.Compounds of this type are also widely employed as synthetic intermediates and metal ligands.…”

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

“…Aliphatic alkenes gave much lower product yields (Scheme 129). 225 The Li group reported phosphonyl radical initiated phosphonofluorination of alkenes. Phosphonyl radical generated from the reaction of diethyl phosphite with AgNO 3 was added to alkenes followed by fluorination with Selectfluor TM to afford the bifunctionalized products 303 (Scheme 130).…”