Chemoselective aerobic oxidation of unprotected diols catalyzed by Pd-(NHC) (NHC = N-heterocyclic carbene) complexes

被引：18
作者：
Bettucci, Lorenzo [1 ]
Bianchini, Claudio [1 ]
Oberhauser, Werner [1 ]
Hsiao, Tsun-Hung [2 ]
Lee, Hon Man [2 ]
机构：
[1] ICCOM CNR, Area Ric CNR Firenze, I-50019 Sesto Fiorentino, Italy
[2] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2010年 / 322卷 / 1-2期
关键词：
Chemoselective oxidation; Diols; Palladium; N-heterocyclic carbenes; PI-ALLYL COMPLEXES; SELECTIVE OXIDATION; SECONDARY ALCOHOLS; MOLECULAR-OXYGEN; PALLADIUM COMPLEXES; HYDROGEN-PEROXIDE; BUCHWALD-HARTWIG; SUBSTRATE SCOPE; SUZUKI-MIYAURA; KETONES;
D O I：
10.1016/j.molcata.2010.02.016
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Neutral Pd(X)(eta(3)-allyl) (X = Cl, OAc (acetate)) complexes bearing mono-coordinating NHC ligands have been synthesized, characterized and employed to catalyze the aerobic oxidation of unprotected 1,2- and 1,3-diols selectively to hydroxy ketones. A comparison of the catalytic performance of these precursors with a reference system has shown that the precursor with the ligands N,N'-bis(adamantyl)imidazol-2-ylidene and chloride is the most efficient for the chemoselective oxidation of 1,2-diols is concerned. High-pressure H-1 NMR (HPNMR) experiments in combination with catalytic batch reactions have provided valuable information on the activation of the precursor as well as on the stability of the catalysts. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码：63 / 72
页数：10
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