ArticleNature communications2024
Ni(II)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons via 1,5-metalate shift.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Cu-Catalyzed dynamic kinetic asymmetric allylation enabled enantioselective assembly of sterically congested triaryl tertiary alcohols.Nature communications · 2026Article
- Lactam enables remote boronate rearrangements to C═N bonds.Communications chemistry · 2026Article
- Alkenyl- and Aryl-Borane Nucleophiles in Enantioselective Iridium-Catalyzed Allylic Substitution of Vinyl Epoxides.Journal of the American Chemical Society · 2025Article
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5 authors.
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Abstract
Chiral tertiary alcohols are an important structural motif, however, the general and efficient methodologies for their synthesis are less reported. Herein, we report a Ni(ІІ)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons under air via a 1,5-metalate shift strategy to obtain chiral tertiary allylic alcohols and diaryl alcohols. The reaction demonstrates good functional group tolerance and delivers chiral tertiary alcohols with good to excellent results. Furthermore, this method can be applied to the late-stage modification of drugs and the efficient synthesis of natural products. Notably, the reaction proceeds through an outer-sphere mechanism. The Ni(II) complex functions both as a Lewis acid to activate the ketone and create a chiral environment, and as coordination bridge linking the ketone and the organoboron-derived "ate" complex, facilitating the 1,5-metalate shift without forming a C-Ni bond. This approach contrasts with traditional transition metal-catalyzed nucleophilic addition reactions that involve carbon-metal bond formation.
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