Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids

Morgan, Dáiríne M.; Lam, Hon Wai; Guiry, Patrick J.

Abstract

Herein we report a syn-arylnickelative cyclisation with ketone- and imine-tethered terminal alkynes (16 examples) in yields of up to 89 %. The reaction proceeds via a syn-aryl nickelation of a terminal alkyne followed by cyclisation of the resulting alkenylnickel species onto the ketone or imine. The enantioselective version of this transformation has also been explored with enantioselectivities of up to 83 : 17 er observed.

Citation

Morgan, D. M., Lam, H. W., & Guiry, P. J. (2024). Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids. European Journal of Organic Chemistry, 27(23), Article e202400445. https://doi.org/10.1002/ejoc.202400445

• Journal Article Type: Article
• Acceptance Date: Apr 26, 2024
• Online Publication Date: May 17, 2024
• Publication Date: Jun 17, 2024
• Deposit Date: May 16, 2024
• Publicly Available Date: May 28, 2024
• Journal: European Journal of Organic Chemistry
• Print ISSN: 1434-193X
• Electronic ISSN: 1099-0690
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 27
• Issue: 23
• Article Number: e202400445
• DOI: https://doi.org/10.1002/ejoc.202400445
• Keywords: nickel catalysis; syn-selective arylnickelation; tethered electrophile; domino reaction
• Public URL: https://nottingham-repository.worktribe.com/output/34849584
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400445