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Dealkenylative Thiylation of C(sp3)–C(sp2) Bonds

preprint
submitted on 10.07.2019, 01:40 and posted on 10.07.2019, 14:24 by Andrew Smaligo, Ohyun Kwon
Carbon–carbon bond fragmentations are useful methods for the functionalization of molecules. The value of such cleavage events is maximized when paired with a subsequent bond formation. Herein we report a protocol for the cleavage of a C(sp3)–C(sp2) bond, followed by the formation of a new C(sp3)–S bond. This reaction is performed in non-anhydrous solvent and open to the air, employs common starting materials, and can be used to rapidly diversify natural products. We have also subjected the thiylated products to various synthetic transformations, demonstrating their utility as synthetic intermediates.

Funding

Phosphine-Catalyzed Annulations and their Applications

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

ohyun@chem.ucla.edu

Institution

UCLA

Country

USA

ORCID For Submitting Author

0000-0002-5405-3971

Declaration of Conflict of Interest

No conflict of interest

Version Notes

version 1.0

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in Organic Letters

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