Palladium-catalysed intramolecular direct arylation of 2-bromobenzenesulfonic acid derivatives

Bheeter, Charles Beromeo ; Bera, Jitendra K. ; Doucet, Henri (2012) Palladium-catalysed intramolecular direct arylation of 2-bromobenzenesulfonic acid derivatives Advanced Synthesis & Catalysis, 354 (18). pp. 3533-3538. ISSN 1615-4150

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/adsc.20...

Related URL: http://dx.doi.org/10.1002/adsc.201200793

Abstract

A palladium-catalysed intramolecular direct arylation of 2-bromobenzenesulfonic acid derivatives was found to proceed using 1 mol% of palladium acetate as the catalyst. The influence of the substituents on the phenol moiety of 2-bromobenzenesulfonic acid phenyl esters reveals that electron-donating substituents favour the reaction while electron-withdrawing ones are unfavourable. The reactivity of sulfonamides was also studied and, in all cases, a selective activation at sp2 C─H vs. sp3 C─H was observed. A sulfonamide bearing both phenyl and benzyl substituents on nitrogen gave selectively the six-membered ring product.

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