Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C-N bond forming reactions with enolizable heterocycles under microwave enhanced conditionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c3nj01355c

• Main Authors: Abdul Khader, K. K, Sajith, Ayyiliath. M, Syed Ali Padusha, M, Nagaswarupa, H. P, Muralidharan, A
• Format: Article
• Language: English
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c3nj01355c

Microwave-mediated, palladium catalyzed C-N bond forming reactions with activated cycloalkenyl nonaflates and enolizable heterocycles using cesium carbonate as a base and a catalytic system employing Pd(OAc) 2 /Xantphos or Pd(OAc) 2 /dppp were found to be effective in driving the reactions to completion. This method resulted in good to excellent yields of the coupled products (22 examples, 25-90%) in short reaction time (30-60 min). Under optimum conditions, cycloalkenyl nonaflates were found to be an effective alternative to analogous triflates in C-N bond forming processes due to their increased stability under the reaction conditions. The use of tetrabutylammonium bromide (Bu 4 NBr) as an additive in these transformations proved to be effective and resulted in better yields of the coupled products. An efficient protocol for Pd catalysed cross-coupling reactions of cycloalkenyl nonaflates is reported.