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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

Authors

Simone M. Gillbard

Chieh-Hsu Chung

Somnath Narayan Karad

Heena Panchal

William Lewis

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



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.

Journal Article Type Article
Publication Date Oct 25, 2018
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
APA6 Citation Gillbard, S. M., Chung, C., 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. doi:10.1039/c8cc06649c
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
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2018/CC/C8CC06649C#!divAbstract

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