The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.
[figure: see text] A novel route to aryloxyamines via the copper-mediated cross-coupling of N-hydroxyphthalimide and phenylboronic acids is reported. The reaction is mediated by selected copper(I) and (II) salts in the presence of pyridine and is tolerant of several functional groups on the phenylboronic acid. The phthallmide group is removed using hydrazine to afford the corresponding aryloxyamine.
Petrassi
H M
HM
Department of Chemistry and Skaggs Institute of Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, MB12, La Jolla, California 92037, USA.
Sharpless
K B
KB
Kelly
J W
JW
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015195:Drug Design; D006834:Hydrazines / Q000737:chemistry; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry; D010797:Phthalimides / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013329:Structure-Activity Relationship
D000588:Amines; D001897:Boronic Acids; D006834:Hydrazines; D004364:Pharmaceutical Preparations; D010797:Phthalimides; D011725:Pyridines; D003300:Copper; C037437:N-hydroxyphthalimide