Selective palladium catalysed monohydroesterification of diols

Fergusson, Stuart B.; Alper, Howard

doi:10.1039/c39840001349

Cited by 23 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Notably, the combined catalyst system of PdCl 2 and CuCl 2 with THF as solvent also enabled selective monohydroesterification of diols, providing a regioselective access to branchedchain monohydroxy esters. 141 This method could also be applied to the selective hydroesterification of alkynes. 142 In these reactions, terminal alkynes gave rise to unsaturated cis-diesters, while internal alkynes resulted in cis-monoesters.…”

Section: Hydrofunctionalization Of Unsaturatedmentioning

confidence: 99%

A Career in Catalysis: Howard Alper

et al. 2019

View full text Add to dashboard Cite

Still going strong in his seventies, Professor Howard Alper continues to make an impact on chemistry internationally. This Account highlights some of his key scientific achievements in catalysis. What began as a fundamental interest in the chemistry of metal carbonyls and their activity modes, evolved into a versatile program addressing some of the most significant and challenging issues in catalysis. Using well-defined metal carbonyl complexes, he and his lab were able to make fundamental insights into diverse transformations involving the catalytic properties of metal carbonyls, including carbonylative ring expansions. His creative and truly interdisciplinary research in catalysis has also resulted in notable contributions to carbonylation, hydrofunctionalization, and cycloaddition chemistry.

show abstract

Section: Hydrofunctionalization Of Unsaturatedmentioning

confidence: 99%

A Career in Catalysis: Howard Alper

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Alkenes were transformed into branched propionic acids in good yields in the presence of water, oxygen, and HCl. Later, they extended their protocol to the monohydroesterification of diols 15b. As shown in Scheme , the reactions could be conducted under mild conditions (room temperature, 1 bar of CO).…”

Section: Oxidative Carbonylation Of Alkenesmentioning

confidence: 99%

Palladium‐Catalyzed Oxidative Carbonylation Reactions

Wu¹,

Neumann²,

Beller³

2013

ChemSusChem

314

View full text Add to dashboard Cite

Palladium-catalyzed coupling reactions have become a powerful tool for advanced organic synthesis. This type of reaction is of significant value for the preparation of pharmaceuticals, agrochemicals, as well as advanced materials. Both, academic as well as industrial laboratories continuously investigate new applications of the different methodologies. Clearly, this area constitutes one of the major topics in homogeneous catalysis and organic synthesis. Among the different palladium-catalyzed coupling reactions, several carbonylations have been developed and widely used in organic syntheses and are even applied in the pharmaceutical industry on ton-scale. Furthermore, methodologies such as the carbonylative Suzuki and Sonogashira reactions allow for the preparation of interesting building blocks, which can be easily refined further on. Although carbonylative coupling reactions of aryl halides have been well established, palladium-catalyzed oxidative carbonylation reactions are also interesting. Compared with the reactions of aryl halides, oxidative carbonylation reactions offer an interesting pathway. The oxidative addition step could be potentially avoided in oxidative reactions, but only few reviews exist in this area. In this Minireview, we summarize the recent development in the oxidative carbonylation reactions.

show abstract

“…Thus, several mechanistic and theoretical studies have been conducted to find efficient catalysts affording good chemo-and regioselectivity as well as high catalytic activity and stability. The same catalyst was used by Alper and co-workers for the reaction of alkenes with diols, [23] such as ethylene glycol, or formate esters [24] under oxidative and acidic conditions. Primarily, ligand-free catalyst precursors were established.…”

Section: Hydroesterification Of Alkenesmentioning

confidence: 99%

“…[22] In this case, stoichiometric quantities of copper(II) chloride were employed to reoxidize Pd 0 , which precipitated from the reaction mixture. The same catalyst was used by Alper and co-workers for the reaction of alkenes with diols, [23] such as ethylene glycol, or formate esters [24] under oxidative and acidic conditions. Thus, with aromatic alkenes mainly branched chain esters were obtained under atmospheric CO pressure.…”

Section: Hydroesterification Of Alkenesmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylation Reactions of Alkenes and Alkynes

2009

View full text Add to dashboard Cite

Palladium‐catalyzed carbonylation reactions of alkenes and alkynes with different nucleophiles have undergone rapid development ever since the seminal work of Reppe back in the 1930s. Nowadays, a plethora of palladium catalysts and various synthetic protocols are available for the synthesis of valuable carboxylic acids and acrylic acids as well as their derivatives. Herein, we summarize the recent catalyst developments and selected organic applications in this area.

show abstract

Selective palladium catalysed monohydroesterification of diols

Abstract: Olefins react with diols (e.g. ethylene glycol) under oxidative carbonylation and acidic conditions, using palladium and copper(i1) chloride a s catalysts, to give hydroxy esters in good yields; this mild reaction (room temperaure, 1 atm) is a regioselective one.

Cited by 23 publications

References 0 publications

A Career in Catalysis: Howard Alper

A Career in Catalysis: Howard Alper

Palladium‐Catalyzed Oxidative Carbonylation Reactions

Palladium‐Catalyzed Carbonylation Reactions of Alkenes and Alkynes

Contact Info

Product

Resources

About