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

Autor: Duong VK; SSPC, the SFI Research Centre for Pharmaceuticals, Centre for Synthesis & Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland., Horan AM; SSPC, the SFI Research Centre for Pharmaceuticals, Centre for Synthesis & Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland., McGarrigle EM; SSPC, the SFI Research Centre for Pharmaceuticals, Centre for Synthesis & Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Nov 06; Vol. 22 (21), pp. 8451-8457. Date of Electronic Publication: 2020 Oct 22.
DOI: 10.1021/acs.orglett.0c03048
Abstrakt: 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.
Databáze: MEDLINE