ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
ChemRxiv DuongHoranMcGarrigle Manuscript.pdf (658.53 kB)
0/0

Synthesis of Pyridylsulfonium Salts and their Application in Transition Metal-Free Formation of Functionalized Bipyridines

preprint
submitted on 06.05.2020 and posted on 11.05.2020 by Vincent K. Duong, Alexandra M. Horan, Eoghan McGarrigle
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.

Funding

National University of Ireland for a Travelling Studentship (2016)

Irish Research Council for a Postgraduate Scholarship (GOIPG/2017/1306)

History

Email Address of Submitting Author

eoghan.mcgarrigle@ucd.ie

Institution

University College Dublin

Country

Ireland

ORCID For Submitting Author

0000-0001-8160-6431

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Exports

Logo branding

Exports