Journal of Organic Chemistry p. 7234 - 7244 (2017)
Update date:2022-08-03
Topics: Nitration Regioselective Ortho Aromatics Cobalt C(sp2)-H Bond Proton-Coupled Electron Transfer Assistance
Nageswar Rao, Desaboini
Rasheed, Sk.
Raina, Gaurav
Ahmed, Qazi Naveed
Jaladanki, Chaitanya Kumar
Bharatam, Prasad V.
Das, Parthasarathi
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.
View MoreContact:+86 21 34123252
Address:14, 4580 Dushi, Shanghai, China
Wuxi D-Stone International Co., Ltd.
Contact:+86-510-82740567
Address:21F Hengtong Int'l Centre, 215Zhongshan Road, Wuxi, Jiangsu,China
Refine Chemicals Science & Technology Technology Developing Co., Ltd.
Contact:+86-22-87899130
Address:No.12,west keyan road,Tianjin City
Anhui Jiatiansen Agrochemical Co.,Ltd
Contact:15366811918
Address:chemical industrial park,xiangyu town,dongzhi county,anhui,china
hangzhou verychem science and technology co.ltd
website:http://www.verypharm.com
Contact:+86-571-88162785; 88162786
Address:F1502, 753 Shenhua road, Hangzhou, China
Doi:10.1038/nchem.1746
(2013)Doi:10.1016/S0040-4039(00)98069-9
(1990)Doi:10.1002/anie.201008196
(2011)Doi:10.1515/hc-2014-0114
(2014)Doi:10.1002/chem.202102536
(2021)Doi:10.1021/ic200544a
(2011)