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

10 July 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

dealkenylative
thiylation
terpenoid
chiral pool
deconstructive
redox
ozonolysis
iron

Supplementary materials

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