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A Copper-Catalyzed Petasis Reaction for the Synthesis of Tertiary Amines and Amino Esters

Robin Frauenlob, Carlos García, Gary A. Bradshaw, Helen M. Burke and Enda Bergin*

*School of Chemistry, Trinity Biomedical Sciences Institute, University of Dublin, Trinity College, Dublin 2, Ireland, Email: ebergintcd.ie

R. Frauenlob, C. Carcía, G. A. Bradshaw, H. M. Burke, E. Bergin, J. Org. Chem., 2012, 77, 4445-4449.

DOI: 10.1021/jo3003503 (free Supporting Information)



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Abstract

A copper-catalyzed process for the coupling of aldehydes, amines, and boronic acids allows greater reactivity with simple aryl boronic acids and aldehydes that are able to coordinate copper. The system enables petasis reactions to proceed that previously failed. Initial mechanistic studies support a process involving transmetalation from boron to copper.


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proposed catalytic cycle



Key Words

Petasis Reaction


ID: J42-Y2012-1340