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: kmh0515gachon.ac.kr

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

DOI: 10.1021/acs.orglett.9b00751

---

see article for more reactions

Abstract

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.

see article for more examples

---

---

Key Words

nitration, PIFA

---

ID: J54-Y2019