Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Cobalt-Catalyzed Regioselective Ortho C(sp2)-H Bond Nitration of Aromatics through Proton-Coupled Electron Transfer Assistance

Cobalt-Catalyzed Regioselective Ortho C(sp2)-H Bond Nitration of Aromatics through Proton-Coupled Electron Transfer Assistance
Gaurav Raina, Prasad V. Bharatam, Parthasarathi Das, Qazi Naveed Ahmed, Desaboini Nageswar Rao, Chaitanya Kumar Jaladanki, Sk. Rasheed
A cobalt-catalyzed proton-coupled electron transfer (PCET) mediated regioselective ortho-specific nitration of aromatic C(sp2)-H bonds using chelation-assisted removable vicinal diamine directing groups was developed. The reaction proceeded under mild conditions in the presence of Co(OAc)2·4H2O as the catalyst with AgNO2 utilized as the nitro source as well as terminal oxidant in the presence of O2 as an external oxidant. No external base or additives were required for this process. Controlled experiments and mechanistic investigations with DFT calculations revealed that the reaction proceeds through a PCET promoted nitro functional group transfer pathway. Moreover, the produced compounds are valuable and pharmaceutically quite relevant.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00808

DOI: 10.1021/acs.joc.7b00808

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