Publication

Chemoselective Removal of Allylic Protecting Groups Using Water-Soluble Pd(OAc)2/TPPTS Catalyst

1997
Journal Articles

Abstract

The removal of allylic protecting groups promoted by the catalytic system Pd(OAc)(2)/TPPTS has been achieved on bifunctional substrates with complete chemoselectivity and high efficiency, in aqueous media. By lowering the amount of palladium catalyst, substituted allylic carboxylates remained unaffected while allylcarbamates, in the same molecule, were quantitatively removed. When using a biphasic C3H7CN-H2O solvent, the water-soluble catalyst could also differentiate allylcarbonates from dimethylallylcarbamates on diprotected amino alcohols. All these reactions were carried out under mild and neutral conditions which are compatible with a large range of molecules including beta-lactams.

Official source

https://infoscience.epfl.ch/entities/publication/8cc20e41-a38d-48ca-86e6-1afc5ef1d3dd

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1997
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/8cc20e41-a38d-48ca-86e6-1afc5ef1d3dd

About this result

Related concepts (21)

Palladium

Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself named after the epithet of the Greek goddess Athena, acquired by her when she slew Pallas. Palladium, platinum, rhodium, ruthenium, iridium and osmium form a group of elements referred to as the platinum group metals (PGMs).

Catalysis

Catalysis (kəˈtæləsɪs) is the process of change in rate of a chemical reaction by adding a substance known as a catalyst (ˈkætəlɪst). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

Hydroformylation

In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: production capacity reached 6.6 tons in 1995. It is important because aldehydes are easily converted into many secondary products.

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Chemoselective Removal of Allylic Protecting Groups Using Water-Soluble Pd(OAc)2/TPPTS Catalyst

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