Microwave-enhanced copper-catalyzed N-arylation of free and protected amino acids in water.
A microwave-enhanced copper-catalyzed protocol for N-arylation using water as the solvent is reported. This fast transformation allows the reaction between various amino acids or amino acid esters and a diverse set of substituted aryl bromides in less than 40 min, affording good yields of non-protected N-arylated amino acids with only minor racemization (6% or less). In addition, online ESI-MS and MS/MS analysis were used to "fish-out" an anionic Cu-containing amino acid complex directly from an ongoing N-arylation reaction.
Röttger
Svenja
S
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, BMC, Box 574, SE- 751 23 Uppsala, Sweden.
Sjöberg
Per J R
PJ
Larhed
Mats
M
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008872:Microwaves; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water / Q000737:chemistry*
D000596:Amino Acids; D014867:Water; D003300:Copper