Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 34, Pages 7470-7474Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01293b
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Funding
- SERB, New Delhi [EMR/2016/006358]
- Indian Institute of Science
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We reported a novel method for synthesizing trisubstituted furan derivatives through Rh(iii)-catalyzed C-vinyl-H activation, revealing the dual role of Ag salt in Paal-Knorr type cyclization. The products can be converted into alcohol and acid derivatives, serving as useful intermediates in synthesizing biologically active molecules.
We report an Rh(iii)-catalyzed one-pot synthesis of trisubstituted furan derivatives through C-vinyl-H activation of alpha,beta-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.
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