3 years ago

Soft–Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion

Soft–Hard Acid/Base-Controlled,
Oxidative, N-Selective Arylation of Sulfonanilides
via a Nitrenium
Ion
Prasenjit Mal, Saikat Maiti
In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C–C bonds is preferred over the functionalization of C–N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft–hard acid–base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C–N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02841

DOI: 10.1021/acs.joc.7b02841

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