Palladium-catalyzed redox diversified entry to axially chiral styrenes <i>via</i> asymmetric olefination with alkynes.

ABSTRACT: Axially chiral olefins represent an underexplored class of atropoisomers given their conformational flexibility and relatively low configurational stability. Atroposelective access to axially chiral olefins via de novo formation of a chiral axis is challenging. Reported herein is palladium-catalyzed redox-diversified olefination of aryl halides with two classes of bifunctional alkynes based on rational design of catalytic systems. The reductive Heck reaction (hydroarylation) of 1,6-diynes afforded axially chiral dienes using potassium formate as the reductant. In the case of 1-alkynylcyclobutanol substrates, ring strain-driven C-C coupling-olefination gave axially chiral, tetrasubstituted enones as the product. In both coupling systems, the reactions proceeded effectively with high

SUBMITTER: Lin Z 

PROVIDER: S-EPMC12242276 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature