Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates

O'Brien, Luke; Argent, Stephen P.; Ermanis, Kristaps; Lam, Hon Wai

Abstract

Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with allylboronates are reported. Transmetalation of the allylboronate with gold produces nucleophilic allylgold(I) species that add to the 4-position of the azinium ion with complete regioselectivity to give functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Density functional theory (DFT) calculations provided mechanistic insight.

Citation

O'Brien, L., Argent, S. P., Ermanis, K., & Lam, H. W. (2022). Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates. Angewandte Chemie International Edition, 61(22), Article e202202305. https://doi.org/10.1002/anie.202202305

• Journal Article Type: Article
• Acceptance Date: Mar 3, 2022
• Online Publication Date: Mar 25, 2022
• Publication Date: May 23, 2022
• Deposit Date: Mar 29, 2022
• Publicly Available Date: Mar 30, 2022
• Journal: Angewandte Chemie - International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 61
• Issue: 22
• Article Number: e202202305
• DOI: https://doi.org/10.1002/anie.202202305
• Keywords: General Chemistry; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/7655196
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/anie.202202305