Synthesis of Pyridylsulfonium Salts and their Application in Transition Metal-Free Formation of Functionalized Bipyridines
2020
An S-selective
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.
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