Precise Synthesis of Ester-Functionalized Cyclo[6]- and Cyclo[7]furans.

ABSTRACT: Shape-persistent conjugated macrocycles have attracted interest for their unique optoelectronic and self-assembly properties, but the syntheses to obtain these structures can be laborious. In this work, we describe the straightforward synthesis of a recently discovered class of macrocycle, the cyclo[n]furan, using Suzuki-Miyaura cross-coupling of a simple aromatic monomer. We demonstrate that the combination of hexyl 2-bromo-5-(boronic acid pinacol ester)furan-3-carboxylate with tris(dibenzylideneacetone)dipalladium(0), tri-tert-butylphosphonium tetrafluoroborate and cesium fluoride leads to cyclo[6]- and cyclo[7]furan esters in 45% yield (28% and 17%, respectively). Crude ¹H NMR spectroscopy revealed that total conversion to macrocycles was 52 ± 6% over 3 runs, hi

SUBMITTER: Sharma D 

PROVIDER: S-EPMC12313054 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature