Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines.
With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished. [reaction: see text].
Altman
Ryan A
RA
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D001965:Bromides / Q000138:chemical synthesis; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006912:Hydroxyquinolines / Q000138:chemical synthesis*; D007454:Iodides / Q000138:chemical synthesis; D011725:Pyridines / Q000138:chemical synthesis*; D012997:Solvents
D001965:Bromides; D006912:Hydroxyquinolines; D007454:Iodides; D011725:Pyridines; D012997:Solvents; C014047:hydroxypyridines; D003300:Copper