Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Carbon–Phosphorus Bond Formation on Anilines Mediated by a Hypervalent Iodine Reagent

Carbon–Phosphorus Bond Formation on Anilines Mediated by a Hypervalent Iodine Reagent
Sylvain Canesi, Saad Boukercha, Siomenan Coulibali, Elsa Deruer
Substituted anilines containing a sulfonyl group may be oxidized in situ in the presence of methanol and a hypervalent iodine reagent to form an active iminium species. Subsequent addition of phosphines or phosphites in the same pot produces meta-substituted anilines in good yields. This formal C–H bond functionalization is a direct and efficient means of selectively substituting the meta-position of anilines to produce aromatic phosphonium ions or phosphonates.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01595

DOI: 10.1021/acs.joc.7b01595

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