Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 18, Pages 9786-9793Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00856
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Funding
- DST
- SERB project [SR/FT/CS-168/2011]
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Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp(2) or sp(3) carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)(2)S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having Csp(3) carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp(3)-H bond activation in high stereoselectivity. Both benzoylation and alkenylation protocols are metal-free, green, simple, efficient, and tolerate a wide variety of functional groups.
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