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Nickel‐catalyzed intramolecular alkene difunctionalization by ball‐milling

Williams, Matthew T. J., Morrill, Louis C. ORCID: and Browne, Duncan L. ORCID: 2023. Nickel‐catalyzed intramolecular alkene difunctionalization by ball‐milling. Advanced Synthesis & Catalysis 365 (9) , pp. 1477-1484. 10.1002/adsc.202300188

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A mechanochemical nickel‐catalyzed intramolecular difunctionalization reaction of alkene tethered aryl halides with alkyl halides is herein described. This method allows for synthesis of 3,3‐disubstituted heterocycles, namely oxindoles, with shorter reaction times than solution‐phase counterparts. Additionally, this process is solvent minimized, with DMA used in liquid‐assisted grinding (LAG) quantities and circumvents the need for chemical activation of the terminal reductant (manganese) through mechanical grinding. The process can be scaled up to yield over a gram of product and modest enantioinduction is possible by utilizing a chiral PyrOx ligand. image

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Additional Information: License information from Publisher: LICENSE 1: URL:
Publisher: Wiley
ISSN: 1615-4150
Date of First Compliant Deposit: 15 May 2023
Date of Acceptance: 2 April 2023
Last Modified: 15 May 2023 22:51

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