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Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines.

Vincent K DuongAlexandra M HoranEoghan M McGarrigle
Published in: Organic letters (2020)
An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. 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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