Ruthenium-catalyzed hydroxylation of unactivated tertiary C-H bonds.
The combination of catalytic RuCl(3) and pyridine with KBrO(3) as the stoichiometric oxidant is shown to efficiently promote the hydroxylation of unactivated tertiary C-H bonds. Substrates possessing different polar functional groups--ester, epoxide, sulfone, oxazolidinone, carbamate, and sulfamate--are found to engage in this reaction to give alcohol products in yields generally exceeding 50%. As judged based on efficiency, ease of operation, substrate scope, and selectivity toward tertiary C-H centers, the method appears competitive with other C-H hydroxylation processes.
McNeill
Eric
E
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Du Bois
J
J
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D006900:Hydroxylation; D011725:Pyridines / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
D011725:Pyridines; D002244:Carbon; D012428:Ruthenium; D006859:Hydrogen; C023666:pyridine