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Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
Author(s) -
Chen Junting,
Li Jiakun,
Plutschack Matthew B.,
Berger Florian,
Ritter Tobias
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914215
Subject(s) - regioselectivity , electrophile , sulfonium , chemistry , stereoselectivity , selectivity , ruthenium , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , salt (chemistry)
Abstract Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C−H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse‐electron‐demand hetero‐Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium‐ and ruthenium‐catalyzed cross‐coupling reactions to make alkenyl C−C, C−Cl, C−Br, and C−SCF 3 bonds with stereoretention.