D. M. D'Souza, D. Leigh, Marcus Papmeyer
Oct 18, 2012
Citations
0
Influential Citations
9
Citations
Journal
Nature Protocols
Abstract
The synthesis of 5,5′-dibromo-2,2′-bipyridine and 5-bromo-2,2′-bipyridine, useful intermediates for elaboration into more complex ligands through metal-catalyzed coupling reactions, can be efficiently conducted on a multigram scale from inexpensive starting materials. The described procedure is reliably scalable and suitable for the synthesis of tens of grams of 5,5′-dibromo-2,2′-bipyridine. 5-Bromo-2,2′-bipyridine is produced as a minor product. The 5,5′-disubstituted-2,2′-bipyridine motif has excellent coordination properties and is a versatile building block for the synthesis of functional materials (including biodiagnostics, photovoltaics and organic light-emitting diodes) and complex molecular topologies (including catenanes and trefoil and pentafoil knots). The selective stepwise functionalization of 5,5′-dibromo-2,2′-bipyridine by consecutive Stille couplings is therefore illustrated and documented in detail. The synthesis of 5,5′-dibromo-2,2′-bipyridine takes 4–5 d: 1 d to prepare the key intermediate 2,2′-bipyridine dihydrobromide, 3 d for its reaction with bromine in a steel bomb reaction vessel and 8 h to isolate and purify the final product.