Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Using Air

被引：122

作者：

Hanson, Susan K. ^{[1
]}

Wu, Ruilian

Silks, L. A. Pete

机构：

[1] Los Alamos Natl Lab, Div Chem, Los Alamos, NM 87545 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 08期

关键词：

ENANTIOSELECTIVE AEROBIC OXIDATION; INSULIN MIMETIC AGENT; ALPHA-HYDROXY ESTERS; MOLECULAR-OXYGEN; SECONDARY ALCOHOLS; IONIC LIQUIDS; ALDEHYDES; COMPLEXES; CHEMISTRY; MECHANISM;

D O I：

10.1021/ol103107v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition metal-catalyzed aerobic alcohol oxidation is an attractive method for the synthesis of carbonyl compounds, but most catalytic systems feature precious metals and require pure oxygen. The vanadium complex (HQ)(2)V(v)(O)(O(I)Pr) (2 mol %, HQ = 8-quinolinate) and NEt(3) (10 mol %) catalyze the oxidation of benzylic, allylic, and propargylic alcohols with air. The catalyst can be easily prepared under air using commercially available reagents and is effective for a wide range of primary and secondary alcohols.

引用

页码：1908 / 1911

页数：4

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[31] Theoretical and Experimental Studies on Reaction Mechanism for Aerobic Alcohol Oxidation by Supported Ruthenium Hydroxide Catalysts [J].

Nikaidou, Fumiya ;

Ushiyama, Hiroshi ;

Yamaguchi, Kazuya ;

Yamashita, Koichi ;

Mizuno, Noritaka .

JOURNAL OF PHYSICAL CHEMISTRY C, 2010, 114 (24) :10873-10880

[32] Palladium(II)-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen [J].

Nishimura, T ;

Onoue, T ;

Ohe, K ;

Uemura, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6750-6755

[33] From Surface-Inspired Oxovanadium Silsesquioxane Models to Active Catalysts for the Oxidation of Alcohols with O2-The Cinnamic Acid/Metavanadate System [J].

Ohde, Christian ;

Limberg, Christian .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) :6892-6899

[34] (PYRIDINE)BIS(8-QUINOLINATO)OXOVANADIUM(IV) - FREE-RADICAL-LIKE METAL CENTER IN REACTIONS WITH DIOXYGEN, PARA-BENZOQUINONE, AND AROMATIC NITROSO-COMPOUNDS [J].

PASQUALI, M ;

LANDI, A ;

FLORIANI, C .

INORGANIC CHEMISTRY, 1979, 18 (09) :2397-2400

[35] Highly enantioselective aerobic oxidation of α-hydroxyphosphonates catalyzed by chiral vanadyl(V) methoxides bearing N-salicylidene-α-aminocarboxylates [J].

Pawar, Vijay D. ;

Bettigeri, Sampada ;

Weng, Shiue-Shien ;

Kao, Jun-Qi ;

Chen, Chien-Tien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6308-6309

[36] Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen [J].

Punniyamurthy, T ;

Velusamy, S ;

Iqbal, J .

CHEMICAL REVIEWS, 2005, 105 (06) :2329-2363

[37] Vanadium-catalyzed asymmetric oxidation of α-hydroxy esters using molecular oxygen as stoichlometric oxidant [J].

Radosevich, AT ;

Musich, C ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1090-1091

[38] ELECTROCHEMICAL STUDIES OF VANADIUM(III), VANADIUM-(IV), AND VANADIUM-(V) COMPLEXES OF 8-QUINOLINOL IN ACETONITRILE - FORMATION OF A BINUCLEAR MIXED-VALENCE (IV,V) COMPLEX [J].

RIECHEL, TL ;

SAWYER, DT .

INORGANIC CHEMISTRY, 1975, 14 (08) :1869-1875

[39] CRYSTALLOGRAPHIC STUDY OF STRUCTURAL TRANS EFFECT - MOLECULAR-STRUCTURE OF OXOISOPROPOXOBIS(8-HYDROXYQUINOLINATO)VANADIUM(V) [J].

SCHEIDT, WR .

INORGANIC CHEMISTRY, 1973, 12 (08) :1758-1761

[40] Recent advances in homogeneous transition metal-catalyzed aerobic alcohol oxidations [J].

Schultz, Mitchell J. ;

Sigman, Matthew S. .

TETRAHEDRON, 2006, 62 (35) :8227-8241

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