Journal
ORGANIC LETTERS
Volume 18, Issue 17, Pages 4258-4261Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02003
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Funding
- NIH NIGMS [GM073836]
- NSERC
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We report the development of an iron-catalyzed method, for the selective oxyfunctionalization of benzylic C(sp(3))-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trilluoroacetic acid, which deactivates more traditionally reactive C-H sites that are alpha to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
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