Abstract
2,4-Dibromopyridine undergoes a regioselective Suzuki cross-coupling reaction at position 2 with several alkenyl(aryl) boronic acids to render 4-bromo-2-carbon substituted pyridines, difficult to be prepared otherwise, in good yields under palladium catalysis, either Pd(PPh 3) 4/TlOH or Pd 2dba 3/PCy 3/K 3PO 4 at 25 °C. This behavior is explained on the basis of the electrophilic character of both C–Br bonds, being their relative reactivity in 2,4-dibromopyridine similar to that in the corresponding monobromopyridines. In addition, the dicoupled compound 6 is not formed through a double oxidative addition of 2,4-dibromopyridine to Pd(PPh 3).
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