Journal
TETRAHEDRON
Volume 62, Issue 48, Pages 11063-11072Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.09.040
Keywords
2,4-dibromopyridine; Suzuki reaction; regioselectivity; palladium catalysis
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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(PPh3)(4)/TlOH or Pd(2)dba(3)/PCy3/K3PO4 at 25 degrees 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-dibromopyri dine to Pd(PPh3). (c) 2006 Elsevier Ltd. All rights reserved.
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