4.8 Article

Rh(III)-catalyzed highly site- and regio-selective alkenyl C-H activation/annulation of 4-amino-2-quinolones with alkynes via reversible alkyne insertion

Journal

CHEMICAL SCIENCE
Volume 14, Issue 39, Pages 10971-10978

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3sc03987k

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3,4-Fused 2-quinolone frameworks play important roles in natural products and biologically active compounds. Rh(III)-catalyzed alkenyl C-H functionalization of 4-amino-2-quinolones provides an efficient and selective approach to access these structural motifs.
3,4-Fused 2-quinolone frameworks are important structural motifs found in natural products and biologically active compounds. Intermolecular alkenyl C-H activation/annulation of 4-amino-2-quinolone substrates with alkynes is one of the most efficient methods for accessing such structural motifs. However, this is a formidable challenge because 4-amino-2-quinolones have two cleavable C-H bonds: an alkenyl C-H bond at the C3-position and an aromatic C-H bond at the C5-position. Herein, we report the Rh(III)-catalyzed highly site-selective alkenyl C-H functionalization of 4-amino-2-quinolones to afford 3,4-fused 2-quinolones. This method has a wide substrate scope, including unsymmetrical internal alkynes, with complete regioselectivity. Several control experiments using an isolated key intermediate analog suggested that the annulation reaction proceeds via reversible alkyne insertion involving a binuclear Rh complex although alkyne insertion is generally recognized as an irreversible process due to the high activation barrier of the reverse process.

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