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submitted on 06.05.2020 and posted on 11.05.2020by Vincent K. Duong, Alexandra M. Horan, Eoghan McGarrigle
arylation of pyridylsulfides with good functional group tolerance has been
developed. The resulting pyridylsulfonium salts have been used in a scalable
transition metal-free coupling protocol yielding functionalized bipyridine
scaffolds with extensive functional group tolerance and modularity.
Pyridylsulfonium salts were coupled to lithiated pyridines in a sulfur-mediated
synthesis of bipyridines. This modular methodology, permits selective
introduction of functional groups from commercially available pyridyl halides,
furnishing symmetrical and unsymmetrical 2,2’- and 2,3’-bipyridines. Iterative
application of the methodology enabled the synthesis of a functionalized
terpyridine with three different pyridine components.