fulltext.study @t Gmail

Hydroaminomethylation of eugenol with di-n-butylamine catalyzed by rhodium complexes: Bringing light on the promoting effect of Brönsted acids

Paper ID Volume ID Publish Year Pages File Format Full-Text
40717 45863 2012 5 PDF Available
Title
Hydroaminomethylation of eugenol with di-n-butylamine catalyzed by rhodium complexes: Bringing light on the promoting effect of Brönsted acids
Abstract

The hydroaminomethylation of eugenol with di-n-butylamine was performed employing a bis[(1,5-ciclooctadiene)(μ-methoxy)rhodium(I)] as pre-catalyst. In the absence of phosphines, the catalyst was efficient in the process, but the regioselectivity for amines was poor. For phosphine-promoted catalyst, the chemoselectivity at the hydroformylation step improved, but the hydrogenation of enamine intermediates was hampered. The regioselectivity within the class of amines was surprisingly high (>96%) for the linear product. The addition of triflic acid (10–20 mol%) improved significantly the efficiency of HAM. Employing the 2,2′-bis((diphenylphosphino)methyl)-1,1′-binaphthyl as ancillary and triflic acid as a promoter, the linear product was obtained in up to 93% yield.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (90 K)Download as PowerPoint slideHighlights► The hydroaminomethylation of eugenol is reported for the first time. ► New amines are produced with yields reaching 93%. ► Brönsted acids with non-coordinating anions are better promoters. ► Trifluoromethanesulfonic acid is an excellent promoter for hydroaminomethylation.

Keywords
Hydroaminomethylation; Acid promotion; Tandem catalysis; Renewable feedstock
First Page Preview
Hydroaminomethylation of eugenol with di-n-butylamine catalyzed by rhodium complexes: Bringing light on the promoting effect of Brönsted acids
Get Full-Text Now
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
Online Support
Any Questions? feel free to contact us
Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 445–446, 28 November 2012, Pages 204–208
Authors
, , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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
Online Support
Any Questions? feel free to contact us