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

Organic & Biomolecular Chemistry Pub Date: 2021-08-06 DOI: 10.1039/D1OB01293B

Abstract

We report an Rh(III)-catalyzed one-pot synthesis of trisubstituted furan derivatives through Cvinyl–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.

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