Rhodium(iii)-catalyzed synthesis of trisubstituted furans via vinylic C-H bond activation

We report an Rh(iii)-catalyzed one-pot synthesis of trisubstituted furan derivatives through C -H activation of α,β-unsaturated ketones with acrylates. The control study revealed that the Heck-type product obtained undergoes Paal-Knorr type cyclization in the presence of an Ag salt. Hence, the Ag sa...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-09, Vol.19 (34), p.7470-7474
Main Authors: Sherikar, Mahadev Sharanappa, Bettadapur, Kiran R, Lanke, Veeranjaneyulu, Prabhu, Kandikere Ramaiah
Format: Article
Language:English
Subjects:
Acrylates
Biological activity
Catalysts
Chemical synthesis
Furans
Hydrogen bonds
Intermediates
Ketones
Lewis acid
Pesticides
Rhodium
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Summary:We report an Rh(iii)-catalyzed one-pot synthesis of trisubstituted furan derivatives through C -H activation of α,β-unsaturated ketones with acrylates. The control study revealed that the Heck-type product obtained undergoes Paal-Knorr type cyclization in the presence of an Ag salt. Hence, the Ag salt plays a dual role of a halide scavenger and a Lewis acid catalyst for Paal-Knorr type cyclization. The furan product can be transferred into the respective alcohol and acid derivatives which are useful intermediates in synthesizing biologically active molecules.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01293b