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PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp(2))-H or C(sp(3))-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water
- CHANDRASHEKAR, MUDITHANAPELLI;
- Dhorma, Lama Prema;
- Kim, Mi-hyun
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38초록
A novel nitration (via C(sp(3))-N breaking/C(sp(2))-N formation with CH3NO2) mediated by [bis-(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp(2))-H functionalization can shift to an alpha-C(sp(3))-H functionalization (cyanation or oxygenation) of the alpha-C(sp(3))-H of cyclic amines.
키워드
HYPERVALENT IODINE REAGENTS; AROMATIC NITRATION; TERTIARY-AMINES; H FUNCTIONALIZATION; CONJUGATE ADDITION; SODIUM-NITRITE; UREA NITRATE; NITROMETHANE; OXIDATION; ATOM
- 제목
- PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp(2))-H or C(sp(3))-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water
- 저자
- CHANDRASHEKAR, MUDITHANAPELLI; Dhorma, Lama Prema; Kim, Mi-hyun
- 발행일
- 2019-05
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 21
- 호
- 9
- 페이지
- 3098 ~ 3102