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PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water

Chandrashekar Mudithanapelli, Lama Prema Dhorma, Mi-hyun Kim*

*Gachon Institute of Pharmaceutical Science & Department of Pharmacy, College of Pharmacy, Gachon University, 191 Hambakmoeiro, Yeonsu-gu, Incheon 21936, Republic of Korea, Email:

C. Mudithanapelli, L. P. Dhorma, M.-h. Kim, Org. Lett., 2019, 21, 3098-3102.

DOI: 10.1021/acs.orglett.9b00751

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PIFA mediates a nitration of aryl amines in the presence of MeNO2 as solvent and H2O as cosolvent via NO2 transfer. Using H2O as the solvent, the C(sp2)-H functionalization shifts to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.

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Key Words

nitration, PIFA

ID: J54-Y2019