Practical Os/Cu-cocatalyzed air oxidation of allyl and benzyl alcohols at room temperature and atmospheric pressure

被引：62

作者：

Muldoon, J ^{[1
]}

Brown, SN ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 06期

关键词：

D O I：

10.1021/ol025648q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new protocol for the oxidation of primary and secondary allyl and benzyl alcohols at room temperature and using 1 atm of air is described. The procedure uses low loadings of copper salts and osmium tetroxide, which is activated with quinuclidine and prereduced with an alkene. Chemoselectivity for allyl and benzyl alcohols is very high, no overoxidation is observed, and the reaction takes place under neutral conditions.

引用

页码：1043 / 1045

页数：3

共 42 条

[1] CHARACTERISTICS OF IRON PHOSPHATE AS A CATALYST FOR PARTIAL OXIDATION [J].

AI, M ;

MUNEYAMA, E ;

KUNISHIGE, A ;

OHDAN, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (02) :551-556

[2]

AUSTIN RG, 1989, Patent No. 4824969

[3] Selective aerobic oxidation of alcohols with a combination of a polyoxometalate and nitroxyl radical as catalysts [J].

Ben-Daniel, R ;

Alsters, P ;

Neumann, R .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8650-8653

[4] Efficient Mn-Cu and Mn-Co-TEMPO-catalysed oxidation of alcohols into aldehydes and ketones by oxygen under mild conditions [J].

Cecchetto, A ;

Fontana, F ;

Minisci, F ;

Recupero, F .

TETRAHEDRON LETTERS, 2001, 42 (38) :6651-6653

[5] STUDIES ON TRANSITION-METAL OXO-COMPLEXES AND NITRIDO-COMPLEXES .3. COMPLEXES OF OSMIUM TETRAOXIDE WITH TERTIARY-AMINES, AND THEIR REACTIONS WITH ALKENES [J].

CLEARE, MJ ;

HYDES, PC ;

GRIFFITH, WP ;

WRIGHT, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1977, (09) :941-944

[6]

Coleman KS, 1998, EUR J INORG CHEM, P1673

[7] Catalytic oxidation of alcohols into aldehydes and ketones by an osmium-copper bifunctional system using molecular oxygen [J].

Coleman, KS ;

Coppe, M ;

Thomas, C ;

Osborn, JA .

TETRAHEDRON LETTERS, 1999, 40 (19) :3723-3726

[8] STAINING AND FIXATION OF UNSATURATED MEMBRANE LIPIDS BY OSMIUM TETROXIDE - CRYSTAL-STRUCTURE OF A MODEL OSMIUM(VI) DIESTER [J].

COLLIN, R ;

GRIFFITH, WP ;

PHILLIPS, FL ;

SKAPSKI, AC .

BIOCHIMICA ET BIOPHYSICA ACTA, 1974, 354 (01) :152-154

[9] Efficient ruthenium-TEMPO-catalysed aerobic oxidation of aliphatic alcohols into aldehydes and ketones [J].

Dijksman, A ;

Arends, IWCE ;

Sheldon, RA .

CHEMICAL COMMUNICATIONS, 1999, (16) :1591-1592

[10] Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].

Dijksman, A ;

Marino-González, A ;

Payeras, AMI ;

Arends, IWCE ;

Sheldon, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833

← 1 2 3 4 5 →