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

页码：63 / 72

页数：10

共 50 条

[31] Synergistic Ligand Effect between N-Heterocyclic Carbene (NHC) and Bicyclic Phosphoramidite (Briphos) Ligands in Pd-Catalyzed Amination
Kim, Miji
Shin, Taeil
Lee, Ansoo
Kim, Hyunwoo
ORGANOMETALLICS, 2018, 37 (19) : 3253 - 3258
[32] 2-Morpholinoethyl-substituted N-heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties
Aktas, Aydin
Kelestemur, Unzile
Gok, Yetkin
Balcioglu, Sevgi
Ates, Burhan
Aygun, Muhittin
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (01) : 131 - 139
[33] Hydrogenation of C-C Multiple Bonds Mediated by [Pd(NHC)(PCy3)] (NHC=N-Heterocyclic Carbene) under Mild Reaction Conditions
Jurcik, Vaclav
Nolan, Steven P.
Cazin, Catherine S. J.
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (11) : 2509 - 2511
[34] Development of N-Heterocyclic Carbene (NHC)-palladium Complex Catalyst and Immobilized NHC-palladium Complex Catalyst
Mizusaki, Tomoteru
JOURNAL OF THE JAPAN PETROLEUM INSTITUTE, 2023, 66 (01) : 1 - 7
[35] The Role of Free N-Heterocyclic Carbene (NHC) in the Catalytic Dehydrogenation of Ammonia-Borane in the Nickel NHC System
Zimmerman, Paul M.
Paul, Ankan
Zhang, Zhiyong
Musgrave, Charles B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) : 2201 - 2205
[36] Insights into the N-Heterocyclic Carbene (NHC)-Catalyzed Intramolecular Cyclization of Aldimines: General Mechanism and Role of Catalyst
Li, Xue
Tang, Mingsheng
Wang, Yanyan
Wang, Yang
Li, Zhongjun
Qu, Ling-Bo
Wei, Donghui
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (13) : 1710 - 1718
[37] Stereoelectronic parameters associated with N-heterocyclic carbene (NHC) ligands:: A quest for understanding
Diez-Gonzalez, Silvia
Nolan, Steven P.
COORDINATION CHEMISTRY REVIEWS, 2007, 251 (5-6) : 874 - 883
[38] Stabilization of organometallic species achieved by the use of N-heterocyclic carbene (NHC) ligands
Scott, NM
Nolan, SP
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (10) : 1815 - 1828
[39] Suzuki-Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes
Buchspies, Jonathan
Rahman, Md Mahbubur
Szostak, Michal
CATALYSTS, 2020, 10 (04)
[40] A Facile Route to Backbone-Tethered N-Heterocyclic Carbene (NHC) Ligands via NHC to aNHC Rearrangement in NHC Silicon Halide Adducts
Schneider, Heidi
Schmidt, David
Radius, Udo
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (07) : 2793 - 2797

← 1 2 3 4 5 →