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One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

Paper ID Volume ID Publish Year Pages File Format Full-Text
52102 46865 2008 5 PDF Available
Title
One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)
Abstract

In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10–24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.

Keywords
Limonene; Hydroformylation; Hydroaminomethylation; Terpenes; Secondary amines; Tertiary amines
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One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 9, Issue 6, 31 March 2008, Pages 1066–1070
Authors
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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