TY - JOUR
T1 - Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine
T2 - Evidence for the role of Pd nanoparticles
AU - Pun, Doris
AU - Diao, Tianning
AU - Stahl, Shannon S.
PY - 2013/6/5
Y1 - 2013/6/5
N2 - We have carried out a mechanistic investigation of aerobic dehydrogenation of cyclohexanones and cyclohexenones to phenols with a Pd(TFA) 2/2-dimethylaminopyridine catalyst system. Numerous experimental methods, including kinetic studies, filtration tests, Hg poisoning experiments, transmission electron microscopy, and dynamic light scattering, provide compelling evidence that the initial PdII catalyst mediates the first dehydrogenation of cyclohexanone to cyclohexenone, after which it evolves into soluble Pd nanoparticles that retain catalytic activity. This nanoparticle formation and stabilization is facilitated by each of the components in the catalytic reaction, including the ligand, TsOH, DMSO, substrate, and cyclohexenone intermediate.
AB - We have carried out a mechanistic investigation of aerobic dehydrogenation of cyclohexanones and cyclohexenones to phenols with a Pd(TFA) 2/2-dimethylaminopyridine catalyst system. Numerous experimental methods, including kinetic studies, filtration tests, Hg poisoning experiments, transmission electron microscopy, and dynamic light scattering, provide compelling evidence that the initial PdII catalyst mediates the first dehydrogenation of cyclohexanone to cyclohexenone, after which it evolves into soluble Pd nanoparticles that retain catalytic activity. This nanoparticle formation and stabilization is facilitated by each of the components in the catalytic reaction, including the ligand, TsOH, DMSO, substrate, and cyclohexenone intermediate.
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U2 - 10.1021/ja403165u
DO - 10.1021/ja403165u
M3 - Article
C2 - 23662607
AN - SCOPUS:84878645169
SN - 0002-7863
VL - 135
SP - 8213
EP - 8221
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 22
ER -