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Synthesis 2022; 54(19): 4329-4338
DOI: 10.1055/a-1866-7737
DOI: 10.1055/a-1866-7737
paper
Palladium/Norbornene-Cocatalyzed Three-Component Synthesis of ortho-Acylated Benzonitriles
We gratefully acknowledge financial support from the National Natural Science Foundation of China (21476078) and the Science and Technology Commission of Shanghai Municipality (12431900902).
Abstract
A palladium/norbornene-cocatalyzed Catellani-type ortho-C–H-acylation/ipso-cyanation of iodoarenes is developed via a three-component approach using safe and low-toxic sodium carboxylates as the acyl sources and CuCN as the CN source, affording the desired products in yields of 50–94%. Without introducing a directing group on the substrate, a catalytic amount of norbornene and palladium can regioselectively activate the ortho-C–H bonds of iodoarenes. The reaction exhibits good functional group tolerance and works well on gram-scale. In addition, this transformation allows rapid and convenient access toward isoindolinones, 1,4-dicarbonyl compounds and ortho-aminated benzonitriles by manipulation of the cyano and carbonyl groups.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1866-7737.
- Supporting Information
Publication History
Received: 31 March 2022
Accepted after revision: 01 June 2022
Accepted Manuscript online:
01 June 2022
Article published online:
05 July 2022
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