Solvent-free isomerization of allylic alcohols catalyzed by a rhodium catalyst-organic framework

被引：17

作者：

Corkum, Elizabeth G. ^{[1
]}

Kalapugama, Suneth ^{[1
]}

Hass, Michael J. ^{[1
]}

Bergens, Steven H. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

RSC ADVANCES | 2012年 / 2卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

TRANSITION-METAL-COMPLEXES; EFFICIENT REDOX ISOMERIZATION; CARBONYL-COMPOUNDS; ASYMMETRIC ISOMERIZATION; AQUEOUS-MEDIA; ENANTIOSELECTIVE ISOMERIZATION; HETEROGENEOUS CATALYSIS; SATURATED CARBONYLS; RUTHENIUM COMPLEXES; CARBENE COMPLEXES;

D O I：

10.1039/c2ra20197f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The solvent-free isomerization of allylic alcohols is reported using an immobilized rhodium catalyst-organic framework (COF) synthesized from alternating ring-opening metathesis polymerization (altROMP) assembly. The catalyst provided TONs as high as 38 000, with catalyst loadings as low as 0.0025 mol% for the isomerizations. Kinetic resolution of starting allylic alcohol 5 was also observed.

引用

页码：3473 / 3476

页数：4

共 71 条

[1] Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature [J].

Ahlsten, Nanna ;

Lundberg, Helena ;

Martin-Matute, Belen .

GREEN CHEMISTRY, 2010, 12 (09) :1628-1633

[2]

Anastas P., 1998, GREEN CHEM THEORY PR

[3] Sulfonate-Functionalized NHC-Based Ruthenium Catalysts for the Isomerization of Allylic Alcohols in Water. Recyclability Studies [J].

Azua, Arturo ;

Sanz, Sergio ;

Peris, Eduardo .

ORGANOMETALLICS, 2010, 29 (16) :3661-3664

[4] Redox Isomerization of Allylic Alcohols Catalyzed by Osmium and Ruthenium Complexes Containing a Cyclopentadienyl Ligand with a Pendant Amine or Phosphoramidite Group: X-ray Structure of an η3-1-Hydroxyallyl-Metal-Hydride Intermediate [J].

Batuecas, Maria ;

Esteruelas, Miguel A. ;

Garcia-Yebra, Cristina ;

Onate, Enrique .

ORGANOMETALLICS, 2010, 29 (09) :2166-2175

[5] Isomerization of allylic alcohols to carbonyl compounds by aqueous-biphase rhodium catalysis [J].

Bianchini, C ;

Meli, A ;

Oberhauser, W .

NEW JOURNAL OF CHEMISTRY, 2001, 25 (01) :11-12

[6] Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds [J].

Bouziane, Asmae ;

Carboni, Bertrand ;

Bruneau, Christian ;

Carreaux, Francois ;

Renaud, Jean-Luc .

TETRAHEDRON, 2008, 64 (51) :11745-11750

[7] Theoretical study on the mechanism of iron carbonyls mediated isomerization of allylic alcohols to saturated carbonyls [J].

Branchadell, V ;

Crévisy, C ;

Grée, R .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (09) :2062-2067

[8]

Bricout H, 1998, EUR J INORG CHEM, P1739

[9] Bis(allyl)-ruthenium(IV) complexes as highly efficient catalysts for the redox isomerization of allylic alcohols into carbonyl compounds in organic and aqueous media:: Scope, limitations, and theoretical analysis of the mechanism [J].

Cadierno, V ;

García-Garrido, SE ;

Gimeno, J ;

Varela-Alvarez, A ;

Sordo, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1360-1370

[10] Water-soluble ruthenium(II) catalysts [RuCl2(η6-arene)-{P(CH2OH)3}] for isomerization of allylic alcohols and alkyne hydration [J].

Cadierno, V ;

Crochet, P ;

García-Garrido, SE ;

Gimeno, J .

DALTON TRANSACTIONS, 2004, (21) :3635-3641

← 1 2 3 4 5 6 7 8 →