Work

Regioselective and Stereodivergent C–H Functionalization of Internal Alkenes

Year: 2026

Type: article

Abstract: Herein, we introduce a new strategy for the regioselective and stereodivergent C–H functionalization of internal alkenes. We discovered that the regioselectivity of internal alkene thianthrenation is exceptionally electronically sensitive and can be controlled by native allylic and homoallylic functional groups. We also found that both alkenyl thianthrenium stereoisomers can be selectively accessed by using different workup conditions. While thianthrenation is typically stereoretentive, the addition of Cs2CO3 in the workup induces isomerization through reversible conjugate addition. We show that both stereoisomers of the alkenyl linchpins can be readily engaged in stereoretentive cross coupling reactions. This selective thianthrenation-coupling sequence introduces a generalizable platform for stereodefined trisubstituted alkene synthesis.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6c17366

Authors: Elizabeth A. Ryutov, Peter J. Verardi, Song N. Dang, Karina Targos, Leah C. Garman, Zachary K. Wickens

Institution: University of Wisconsin–Madison

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: NIH Office of the Director, National Institute of General Medical Sciences, Division of Chemistry, National Science Foundation Graduate Research Fellowship Program