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Paper | Regular issue | Vol 75, No. 1, 2008, pp.57-64
Published online, 20th September, 2007
DOI: 10.3987/COM-07-11170
Synthesis of 2,4-Dibromopyridine and 4,4’-Dibromo-2,2’-bipyridine. Efficient Usage in Selective Bromine-Substitution under Palladium-Catalysis

Ramón García-Lago, José-Lorenzo Alonso-Gómez, Cristina Sicre, and María-Magdalena Cid*

*Organic Chemistry Department, Universtiy of Vigo, Lagoas-Marcosende, 36310 Vigo, Spain

Abstract

We report an efficient method for preparing 2,4-dibromopyridine and 4,4’-dibromo-2,2’-bipyridine from the corresponding nitroazine N-oxide in one step via a tandem nucleophilic substitution-N-oxide reduction process. The one step preparation of 4,4’-dihalo-2,2’-bipyridines from dihalopyridines via a Stille reaction is also described. 4,4’-Dibromo-2,2’-bipyridine undergoes selective mono- or disubstitution processes under palladium catalysis. This short synthetic procedure is an efficient and reliable process for preparing conjugated pyridine and 2,2’-bipyridine building blocks for applications in coordination chemistry and materials science.