Suzuki-Miyaura cross-coupling is one of the most widely used methods for the coupling of aromatics but has not yet found widespread application in pyridyl coupling at the 2-position due to the rapid protodeborylation of many 2-pyridyl boronic acids and their derivatives. Our group has found application of the Suzuki-Miyaura cross-coupling to synthesize several polypyridyl ligands using air stable 2-pyridyl boronates. Most notably, this method will aid in the synthesis of asymmetric polypridyl ligands. Coupling of substituted pyridines has been demonstrated by the use of this method to synthesize 4-methoxy-2,2′-bipyridine. Once the methoxy-substituted bipyridine has been synthesized, 4-hydroxy-2,2′-bipyridine is accessed via a demethylation. Exploration has also begun on the use of Suzuki coupling to synthesize functionalized terpyridines such as 4′-methoxy-2,2′:6′,2′′-terpyridine and 6,6′′-methoxy-2,2′:6′,2′′-terpyridine.<br/>

Synthesis of functionalized polypyridyl ligands using Suzuki coupling

2019 Spring National Meeting

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