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

Nageswar Rao, Desaboini ; Rasheed, Sk. ; Raina, Gaurav ; Ahmed, Qazi Naveed ; Jaladanki, Chaitanya Kumar ; Bharatam, Prasad V. ; Das, Parthasarathi (2017) Cobalt-Catalyzed Regioselective Ortho C(sp2)-H Bond Nitration of Aromatics through Proton-Coupled Electron Transfer Assistance The Journal of Organic Chemistry, 82 (14). pp. 7234-7244. ISSN 0022-3263

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

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

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:116342
Deposited On:12 Apr 2021 09:25
Last Modified:12 Apr 2021 09:25

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