Ambifunctional cooperative catalysts

Rowlands, Gareth J.

doi:10.1016/s0040-4020(01)00057-6

Cited by 296 publications

(88 citation statements)

References 139 publications

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“…While our own investigations were in progress (as described below), in 2001 Suzuki et al reported [59] that under slightly different conditions, 10 (30 mol %) reacted with 1-octyne to give 35 % of aldehyde and 18 % of alkane, not quite two turnovers (Scheme 6). Significantly, 65 % of the ruthenium was recovered as stable complex 14, isolation of which (like that of related complex 13 by Bruce and co-workers) suggested that catalyst instability was due to loss of phosphine (15,16). Two simple and effective remedies applied by the Japanese team were 1) to use smaller, more donating phosphines such as Me 2 PPh, since these are less likely to dissociate, or 2) to use chelating phosphines, since in that case if one end of the ligand dissociated it would still be attached at the other end.…”

Section: Anti-markovnikov Alkyne Hydrationmentioning

confidence: 74%

Bifunctional Organometallic Catalysts Involving Proton Transfer or Hydrogen Bonding

Grotjahn¹

2005

Chemistry A European J

136

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Section: Anti-markovnikov Alkyne Hydrationmentioning

confidence: 74%

Bifunctional Organometallic Catalysts Involving Proton Transfer or Hydrogen Bonding

Grotjahn¹

2005

Chemistry A European J

136

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“…Current work focuses on the synthesis of various phosphinylated derivatives (with or without the N-side chain) to improve the selectivity and to design ligands suited for hetero-bimetal catalysis. [76,80] Experimental Section…”

Section: Resultsmentioning

confidence: 99%

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

2004

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A number of C 2 -symmetrical geminal bis-(sulfoximine)s have been prepared for the first time and used as ligands in boron-mediated reductions of acetophenone and copper complex-catalyzed 1,4-additions of diethylzinc to 2-cyclohexenone. The copper complex of bis(sulfoximine) 46 was found to be highly active in this type of reaction, furnishing the addition product in nearly quantitative yield even at À 90 8C. From the reaction of bis(sulfoximine) 42 with Cu(OTf) 2 a copper complex was isolated and characterized by X-ray structural analysis. A mixture of SES-Cl and NaN 3 in acetonitrile was found to behave like SES-N 3 in FeCl 2 -mediated iminations of sulfoxides, affording the corresponding sulfoximines with complete retention of the sulfur configuration.

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“…Poor leaving groups such as MeϪO Ϫ are much less easily expelled than the carbamate ion from tetrahedral intermediate 8, which reverts to the reactants. An elaborated catalyst (10) for the methanolysis of α-hydroxy esters (1c) has been devised.…”

Section: Hydrolysis and Methanolysis Of Estersmentioning

confidence: 99%

Catalysis through Induced Intramolecularity: What Can Be Learned by Mimicking Enzymes with Carbonyl Compounds that Covalently Bind Substrates?

Pascal

2003

Eur J Org Chem

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Protein engineering and the use of catalytic antibodies have given substance to the possibility of making artificial enzymes, whereas chemical design has provided functional, though not yet useful, enzyme mimics. This article is devoted to a class of mimics that uses covalent binding to substrates at a site different from the reaction center and that exhibits turnover. These molecular devices are capable of converting the bimolecular reaction of a substrate into a fast intramolecular one and may be defined by the concept of catalysis by induced intramolecularity. As examples of such systems, several reactions of bifunctional substrates that involve catalysis by carbonyl compounds are brought together in this review. Their ability to catalyze difficult reactions such as the hydrolysis of unactivated amides by mimicking enzyme−substrate complementarity is the result of a uniform stabilization of bound species, including both the transition state and also encounter complexes, which is the specific feature of these systems. They allow quantitative analysis of differences be-

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Ambifunctional cooperative catalysts

Cited by 296 publications

References 139 publications

Bifunctional Organometallic Catalysts Involving Proton Transfer or Hydrogen Bonding

Bifunctional Organometallic Catalysts Involving Proton Transfer or Hydrogen Bonding

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

Catalysis through Induced Intramolecularity: What Can Be Learned by Mimicking Enzymes with Carbonyl Compounds that Covalently Bind Substrates?

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