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These are preliminary reports that have not been peer-reviewed.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)

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

preprint
submitted on 06.05.2020, 23:02 and posted on 11.05.2020, 08:01 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