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J Org Chem. 2010 Jun 4;75(11):3916-9. doi: 10.1021/jo1005813.

FeCl3-catalyzed oxidative allylation of sp2 and sp3 C-H bond adjacent to a nitrogen atom: easy access to homoallyl tertiary amines.

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1
Organic Division-III, Indian Institute of Chemical Technology, Hyderabad 500 007, India. gkswamy_iict@yahoo.co.in

Abstract

Oxidative allylation to sp(2)- and sp(3)-carbon attached to the nitrogen atom was accomplished. The alpha-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous (t)BuOOH. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were also allylated through this protocol.

PMID:
20446705
DOI:
10.1021/jo1005813
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