1. Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
- Author
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Biao Ma, Mei-Ling Wang, Hui-Xiong Dai, Han-Yuan Li, Xing Wang, Zhen-Yu Wang, and Hui Xu
- Subjects
chemistry.chemical_classification ,Ketone ,010405 organic chemistry ,Alkene ,Aryl ,Organic Chemistry ,Leaving group ,Alkylation ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Styrene ,chemistry.chemical_compound ,chemistry ,Heck reaction ,Physical and Theoretical Chemistry ,Bond cleavage - Abstract
Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.
- Published
- 2021