Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides

Gillbard, Simone M.; Chung, Chieh-Hsu; Karad, Somnath Narayan; Panchal, Heena; Lewis, William; Lam, Hon Wai

Abstract

The synthesis of multisubstituted pyrroles by the nickel-catalyzed reaction of N-tosylalkynamides with arylboronic acids is reported. These reactions are triggered by alkyne arylnickelation, followed by cyclization of the resulting alkenylnickel species onto the amide. The reversible E/Z isomerization of the alkenylnickel species is critical for cyclization. This method was applied to the synthesis of pyrroles that are precursors to BODIPY derivatives and a biologically active compound.

Citation

Gillbard, S. M., Chung, C.-H., Karad, S. N., Panchal, H., Lewis, W., & Lam, H. W. (2018). Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides. Chemical Communications, 54(83), 11769-11772. https://doi.org/10.1039/c8cc06649c

• Journal Article Type: Article
• Acceptance Date: Sep 21, 2018
• Online Publication Date: Sep 22, 2018
• Publication Date: Oct 25, 2018
• Deposit Date: Sep 22, 2018
• Publicly Available Date: Sep 23, 2019
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Electronic ISSN: 1364-548X
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 54
• Issue: 83
• Pages: 11769-11772
• DOI: https://doi.org/10.1039/c8cc06649c
• Keywords: Materials chemistry; Electronic, Optical and magnetic materials; General chemistry; Surfaces, Coatings and films; Metals and alloys; Ceramics and composites; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/1125482
• Publisher URL: http://pubs.rsc.org/en/Content/ArticleLanding/2018/CC/C8CC06649C#!divAbstract
• Contract Date: Sep 22, 2018