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Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole

Paper ID Volume ID Publish Year Pages File Format Full-Text
39269 45816 2015 7 PDF Available
Title
Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole
Abstract

•Estragole is a by-product of cellulose industry.•The hydroformylation of estragole gives perfumery aldehydes.•The hydroaminomethylation of estragole gives antifungal analogs.•Monophospholes are efficient ancillaries for Rh-promoted hydroaminomethylation.

The hydroaminomethylation (HAM) of estragole, a bio-renewable starting material, with di-n-butylamine was studied for the first time resulting in three novel amines. The process consists of the alkene hydroformylation followed by the in situ reductive amination of primarily formed aldehydes. In order to control chemo- and regioselectivities, three classes of phosphorus(III) compounds were employed as ancillaries for rhodium(I) catalysts: phosphine, phosphites and phospholes. Phosphole-promoted systems have showed the best overall performance, being more selective in the hydrofomylation step than non-promoted or phosphite-promoted systems, as well as more efficient in the reductive amination step than the standard triphenylphosphine based system. It has been found that both the double bond isomerization (a concurrent reaction) and the enamine hydrogenation (the last step in the HAM process) are favored by less electron-donating ligands, with phospholes presenting an excellent compromise to ensure high chemoselectivity and reasonably fast formation of target amines.

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Keywords
Hydroaminomethylation; Hydroformylation; Renewable feedstock; Phospholes; Estragole
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Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 497, May 2015, Pages 10–16
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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Any Questions? feel free to contact us