Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Oxidant-Controlled C-sp2/sp3–H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines

Oxidant-Controlled C-sp2/sp3–H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines
Rohit Sharma, Mohd Abdullaha, Sandip B. Bharate
Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp2 or sp3 carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)2S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having C-sp3 carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp3-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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00856

DOI: 10.1021/acs.joc.7b00856

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