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Sulfones: A New Functional Group for Modular Radical Cross-Coupling

preprint
submitted on 19.12.2017 and posted on 19.12.2017 by Phil Baran, Rohan R. Merchant, Jacob T. Edwards, Tian Qin, Monika M. Kruszyk, Cheng Bi, Guanda Che, Deng-Hui Bao, Wenhua Qiao, Lijie Sun, Michael R. Collins, Gary M. Gallego, James J. Mousseau, Philippe Nuhant
Cross-coupling chemistry comprises the vast majority of reactions employed in the synthesis of medicines, agrochemicals, and other functional materials. The interest in single-electron-induced coupling chemistry stems from the unique ability of these methods to facilitate the formation of challenging C(sp2)–C(sp3) linkages. This work introduces a new functional group, PT sulfones, for radical cross-coupling, enabling the simplified modular assembly of complex structures in an ordered, practical fashion. The scope of this method is extensively explored, and its strategic application is exemplified through the streamlined preparation of medicinally-oriented fluorine-containing scaffolds that previously required multiple steps, toxic reagents, and non-modular retrosynthetic blueprints. This work has also resulted in the development of five reagents for the rapid assembly of a vast set of structures, many of which contain challenging fluorination patterns.

Funding

NIH GM-118176

History

Topic

  • Organic Synthesis and Reactions

Email Address of Submitting Author

pbaran@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0001-9193-9053

Declaration of Conflict of Interest

No conflict of interest to declare

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