Issue 16, 2021

Gold-catalyzed synthesis of 1H-isochromene-4-carbaldehydes via oxidative cascade cyclization

Abstract

An efficient gold-catalyzed formation of indenylidene-derived 1H-isochromene-4-carbaldehydes from substituted 1,5,10-triyne-O-silanes was developed under mild reaction conditions. In this reaction, gold-catalyzed selective oxidation, 1,2-migration, nucleophilic addition and then 5-endo-dig cyclization took place regioselectively. The indenylidene-derived isochromene-4-carbaldehydes were synthesized in moderate to very good yields via the formation of new C–C and C–O bonds in one pot.

Graphical abstract: Gold-catalyzed synthesis of 1H-isochromene-4-carbaldehydes via oxidative cascade cyclization

Supplementary files

Article information

Article type
Paper
Submitted
13 Jan 2021
Accepted
09 Mar 2021
First published
17 Mar 2021

Org. Biomol. Chem., 2021,19, 3634-3643

Gold-catalyzed synthesis of 1H-isochromene-4-carbaldehydes via oxidative cascade cyclization

C. Emmaniel Raju, V. Kadiyala, G. Sreenivasulu, P. B. Kumar, B. Sridhar and G. V. Karunakar, Org. Biomol. Chem., 2021, 19, 3634 DOI: 10.1039/D1OB00066G

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