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

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Summary of "PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp)-H or C(sp)-H: Nitration via C-N Bond Cleavage of CHNO, Cyanation, or Oxygenation in Water."

A novel nitration (via C(sp)-N breaking/C(sp)-N formation with CHNO) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO transfer from CHNO 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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Name: Organic letters
ISSN: 1523-7052


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