Issue 29, 2015

DMSO/I2 mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

Abstract

A novel and efficient I2/DMSO mediated metal-free strategy is presented for the direct C–C bond cleavage of aryl-/heteroaryl- or aliphatic α-ketoaldehydes by C2-decarbonylation and C1-carbonyl oxidation to give the corresponding carboxylic acids followed by esterification in one pot, offering excellent yields in both the steps. Here, DMSO acts as the oxygen source/oxidant and this reaction works very well under both conventional heating and microwave irradiation. This is a very simple and convenient protocol.

Graphical abstract: DMSO/I2 mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

Supplementary files

Article information

Article type
Paper
Submitted
20 May 2015
Accepted
17 Jun 2015
First published
17 Jun 2015

Org. Biomol. Chem., 2015,13, 7973-7978

Author version available

DMSO/I2 mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

V. Venkateswarlu, K. A. Aravinda Kumar, S. Gupta, D. Singh, R. A. Vishwakarma and S. D. Sawant, Org. Biomol. Chem., 2015, 13, 7973 DOI: 10.1039/C5OB01015B

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