Journal
ACS CATALYSIS
Volume 3, Issue 11, Pages 2599-2605Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs400689a
Keywords
alcohol oxidation; aerobic; kinetics; copper; TEMPO; mechanism
Categories
Funding
- U.S. Department of Energy [DE-FG02-05ER15690]
- ACS GCI Pharmaceutical Roundtable
- Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry
- National Institutes of Health [CBIT NIGMS T32 GM008505, S10 RR08389]
- National Science Foundation [CHE-9208463]
- U.S. Department of Energy (DOE) [DE-FG02-05ER15690] Funding Source: U.S. Department of Energy (DOE)
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Combinations of homogeneous Cu salts and 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) have emerged as practical and efficient catalysts for the aerobic oxidation of alcohols. Several closely related catalyst systems have been reported, which differ in the identity of the solvent, the presence of 2,2'-bipyridine as a ligand, the identity of basic additives, and the oxidation state of the Cu source. These changes have a significant influence on the reaction rates, yields, and substrate scope. In this report, we probe the mechanistic basis for differences among four different Cu/TEMPO catalyst systems and elucidate the features that contribute to efficient oxidation of aliphatic alcohols.
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