Issue 7, 2020

Rh-Catalyzed aldehydic C–H alkynylation and annulation

Abstract

Novel Rh-catalyzed aldehydic C–H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C–H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-dibromoalkene followed by annulation. This protocol shows good functional group tolerance including aryl, alkenyl, alkyl and heteroaryl-1,1-dibromoalkenes. The steric/electronic effect was demonstrated during the base-mediated in situ cyclization of o-hydroxyynones to generate aurones.

Graphical abstract: Rh-Catalyzed aldehydic C–H alkynylation and annulation

Supplementary files

Article information

Article type
Paper
Submitted
16 Dec 2019
Accepted
23 Jan 2020
First published
31 Jan 2020

Org. Biomol. Chem., 2020,18, 1402-1411

Rh-Catalyzed aldehydic C–H alkynylation and annulation

M. L. N. Rao and B. S. Ramakrishna, Org. Biomol. Chem., 2020, 18, 1402 DOI: 10.1039/C9OB02670C

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