Rhodium(iii)-catalysed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids: synthesis of benzofuran-2(3H)-ones.

doi:10.1039/c9ob01553a

Paper

Rhodium(iii)-catalysed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids: synthesis of benzofuran-2(3H)-ones.

Published Sep 25, 2019 · Jin-Long Pan, Tuan-Qing Liu, Chao Chen

Organic & biomolecular chemistry

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Abstract

Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).

Study Snapshot

Rhodium(iii)-catalyzed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids yields benzofuran-2(3H)-ones, offering a regio- and

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Rhodium(iii)-catalysed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids: synthesis of benzofuran-2(3H)-ones.

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References

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Citations

DFT and experimental studies on Rh(III)-catalyzed dual directing-groups-assisted [3+2] annulation and ring-opening of N‑aryloxyacetamides with 1-(phenylethynyl)cycloalkanol

Rh(III) catalyzes the cascade [3+2] annulation and ring-opening reaction of N-aryloxyacetamides with 1-(phenylethynyl)cyclobutanol, with the 4-membered ring being critical for high ring strain

Transition Metal Promoted Cascade Heterocycles Synthesis via C-H Functionalization.

Transition metal-mediated C-H activation triggers cascade reactions for heterocycle synthesis, offering a unique approach for synthesis of complex heterocycles.