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-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.

Automated summary

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.