Comparison of cationic rhodium and iridium complexes in directed homogeneous hydrogenation

Brown, John M.; Hall, Stephen A.

doi:10.1016/s0040-4020(01)82359-0

Cited by 23 publications

(8 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[Ir(cod)(PPh 2 Me) 2 ]PF 6 , [Ir(cod)(PPh 3 ) 2 ]PF 6 , [Ir(cod)(PCy 3 )(Py)]PF 6 , and [Ir(cod) 2 ]PF 6 15 were prepared by the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of Silyl Enol Ethers via the Iridium-Catalyzed Isomerization of Allyl Silyl Ethers

1998

View full text Add to dashboard Cite

The stereoselective isomerization of allyl silyl ethers to (E)- or (Z)-silyl enol ethers was carried out in the presence of a cationic iridium(I) catalyst. The complex, prepared in situ by treating [Ir(cod)2]PF6/2PPr3 with hydrogen, was found to be an excellent catalyst for the isomerization of primary and secondary allyl ethers in high yields. The primary allyl silyl ethers produced (E)-enol ethers and the secondary allyl ethers afforded (Z)-enol ethers with high stereoselectivity, often exceeding 99%.

show abstract

“…[Ir(cod)(PPh 2 Me) 2 ]PF 6 , [Ir(cod)(PPh 3 ) 2 ]PF 6 , [Ir(cod)(PCy 3 )(Py)]PF 6 , and [Ir(cod) 2 ]PF 6 15 were prepared by the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of Silyl Enol Ethers via the Iridium-Catalyzed Isomerization of Allyl Silyl Ethers

1998

View full text Add to dashboard Cite

show abstract

“…92 3 ] affords a good catalytic system for the hydrogenation of alkenes conjugated with aromatic groups, including furans, thiophenes and heterocycles, carboxylic acids, esters, lactones, amides, nitriles, aldehydes, ketones, and nitro compounds. 10,11,41,42 In the last case, the nitro group is not reduced. 94 With aldehydes, decarbonylation can sometimes occur.…”

Section: Dienes To Alkenes By 14-reductionmentioning

confidence: 99%

8.17 Homogeneous Catalytic Hydrogenation of CåC and CåC

Ager¹

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

“…In entries 6, 7 and 8, the directivity of the hydroxyl group at the bishomoallylic position effectively overrides the effect of the carbamate unit [38]. In the hydrogenation of methylenebicyclo[2.2.2]octan-2-ol, the exo hydroxyl group does not serve as a directive group, and stereorandom hydrogenation proceeds contrary to the hydrogenation of methylenebicyclo[2.2.2]octan-2-ol with an endo hydroxyl group (entries 9 and 10) [29]. In entry 11 of Table 21.5, the methylenebicyclo[2.2.2]octane compound is hydrogenated in lower selectivity but at a higher rate than the parent alcohol with rhodium catalyst [29].…”

mentioning

confidence: 99%

“…In the hydrogenation of methylenebicyclo[2.2.2]octan-2-ol, the exo hydroxyl group does not serve as a directive group, and stereorandom hydrogenation proceeds contrary to the hydrogenation of methylenebicyclo[2.2.2]octan-2-ol with an endo hydroxyl group (entries 9 and 10) [29]. In entry 11 of Table 21.5, the methylenebicyclo[2.2.2]octane compound is hydrogenated in lower selectivity but at a higher rate than the parent alcohol with rhodium catalyst [29]. Other functional groups which have a heteroatom rather than a hydroxyl group capable of directing the hydrogenation include alkoxyl, alkoxycarbonyl, carboxylate, amide, carbamate, and sulfoxide.…”

mentioning

confidence: 99%