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

We report an Rh( iii )-catalyzed one-pot synthesis of trisubstituted furan derivatives through C vinyl -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, t...

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Published in:Organic & biomolecular chemistry 2021-09, Vol.19 (34), p.747-7474
Main Authors: Sherikar, Mahadev Sharanappa, Bettadapur, Kiran R, Lanke, Veeranjaneyulu, Prabhu, Kandikere Ramaiah
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Summary:We report an Rh( iii )-catalyzed one-pot synthesis of trisubstituted furan derivatives through C vinyl -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. A simple method for the synthesis of trisubstituted furans has been disclosed using an Rh( iii )-catalyst by C vinyl -H bond activation, with silver salt Ag( i ) is playing a dual role - a halide scavenger and a Lewis acid catalyst for promoting Paal-Knorr type cyclization.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01293b