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Synlett 2023; 34(15): 1809-1813
DOI: 10.1055/a-2047-9575
letter

Use of Carbonyldiimidazole as an Activator of Formic Acid in a Tris(dibenzylideneacetone)dipalladium-Catalyzed Formylation of Aryl Iodides

Sundar Nadhagopal
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb Research Center (BBRC), Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India
,
Zulelal Dolas
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb Research Center (BBRC), Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India
,
Arundutt Silamkoti
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb Research Center (BBRC), Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India
,
Anuradha Gupta
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb Research Center (BBRC), Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India
,
Arvind Mathur
b   Small Molecule Drug Discovery, Research and Early Development, Bristol Myers Squibb, P.O. Box 4000, Princeton, New Jersey 08543-4000, USA
,
Sukhen Karmakar∗
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb Research Center (BBRC), Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India
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Abstract

A carbonyldiimidazole (CDI)-promoted generation of CO from formic acid has been exploited in a reductive formylation of aryl iodides in the presence of tris(dibenzylideneacetone)dipalladium. The reaction conditions are mild with a broad functional-group tolerance that includes keto, bromo, nitrile, ester, and nitro groups. In the reaction pathway, CDI reacts with formic acid to generate a formyl imidazole that ultimately produces the CO needed for the formylation process on the activated arylpalladium complex.

Key words

formylation - carbonyldiimidazole - formic acid - palladium catalysis - aryl aldehydes - aryl iodides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2047-9575.
  • Supporting Information


Publication History

Received: 02 December 2022

Accepted after revision: 06 March 2023

Accepted Manuscript online:
06 March 2023

Article published online:
12 April 2023

© 2023. Thieme. All rights reserved

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