NDLI: Rhodium catalyzed hydroformylation of nerolidol

Content Provider	Royal Society of Chemistry (RSC)
Author	Gusevskaya, Elena V. Freitas, Marina C. de Faria, Amanda de Camargo Oliveira, Kelley C. B. de Santos, Eduardo N. dos
Copyright Year	2014
Abstract	The rhodium-catalyzed hydroformylation of nerolidol, a biorenewable substrate with strong therapeutic potential available from various essential oils, was studied in toluene and ethanol solutions in the presence of PPh3 or P(O-o-tBuPh)3 ligands. In toluene, the reaction gave with high chemo- and stereoselectivity a cyclic hemiacetal, which formally arises from the intramolecular cyclization of the primarily formed hydroxy aldehyde. In ethanol, hydroformylation gave a corresponding cyclic acetal in excellent yields even without additional acid co-catalysts. In the absence of phosphorous ligands, nerolidol was resistant to hydroformylation probably due to binding with rhodium through both the double bond and the hydroxyl group to form stable chelates. The P(O-o-tBuPh)3 ligand exerted a remarkable effect on the substrate reactivity accelerating the reaction by five to ten times as compared to the system with PPh3. All isolated products have a pleasant sweet floral and woody scent and can be useful as components of synthetic fragrances.
Starting Page	1954
Ending Page	1959
Page Count	6
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	4
Issue Number	7
Journal	Catalysis Science & Technology
DOI	10.1039/c3cy01104f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ligand Toluene Alcohol Hemiacetal Renewable resource Aldehyde Stereoselectivity Acetal Hydroxy group Alkene Rhodium Carboxylic acid Hydroformylation
Content Type	Text
Resource Type	Article
Subject	Catalysis

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