Copper-catalyzed α-amination of phosphonates and phosphine oxides: a direct approach to α-amino phosphonic acids and derivatives.
A direct approach to important α-amino phosphonic acids and its derivatives has been developed by using copper-catalyzed electrophilic amination of α-phosphonate zincates with O-acyl hydroxylamines. This amination provides the first example of CN bond formation which directly introduces acyclic and cyclic amines to the α-position of phosphonates in one step. The reaction is readily promoted at room temperature with as little as 0.5 mol % of catalyst, and demonstrates high efficiency on a broad substrate scope.
Department of Chemistry, Duke University, Durham, NC 27708-0346 (USA).
Stacey L
SL
McDonald
Qiu
Q
Wang
D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010757:Phosphorous Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D063065:Organophosphonates; D010087:Oxides; D010757:Phosphorous Acids; D003300:Copper
CH functionalization; amination; amines; copper; zinc