PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp 2 )-H or C(sp 3 )-H: Nitration via C-N Bond Cleavage of CH 3 NO 2 , Cyanation, or Oxygenation in Water
A novel nitration (via C(sp )-N breaking/C(sp )-N formation with CH NO ) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO transfer from CH NO to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent...
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| Published in | Organic letters Vol. 21; no. 9; pp. 3098 - 3102 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
03.05.2019
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| Online Access | Get full text |
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| Summary: | A novel nitration (via C(sp
)-N breaking/C(sp
)-N formation with CH
NO
) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO
transfer from CH
NO
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
)-H functionalization can shift to an α-C(sp
)-H functionalization (cyanation or oxygenation) of the α-C(sp
)-H of cyclic amines. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.9b00751 |