Chemodivergent Synthesis of Benzofurans and 2,3-Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes

Author summary

Chemodivergent synthesis of benzofurans and 2,3-dihydrobenzofurans has been realized. Under a reaction system consisting of DBDMH and K₂CO₃ as promotors, controlled conditions enabled the formation of two sets of valuable heterocycles from the tandem transformation of enaminones and salicylaldehydes. The key to success was the identification of the reaction parameters, in which the imine intermediate which was formed by transient halogenation coupling and substitution processes underwent either aldol condensation/annulation or imine hydrolysis/aldol condensation. The additives NH₄Cl or Fe₂(SO₄)₃ controlled the unique selectivity of this reaction. A broad substrate scope of enaminones and salicylaldehydes has been employed in this reaction, demonstrating excellent functional group tolerance and versatility.

Keywords

Cross-coupling / Umpolung / Domino reactions / Enaminone / Benzofurans / 2,3-Dihydrobenzofurans

RIGHTS & PERMISSIONS

2024 2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH