Rhodium(i)-catalyzed cascade C(sp 2 )-H bond alkylation - amidation of anilines: phosphorus as traceless directing group.
| Autor: | Peng M; Univ. Rennes, CNRS UMR6226 Rennes F-3500 France., Ari D; Univ. Rennes, CNRS UMR6226 Rennes F-3500 France., Roisnel T; Univ. Rennes, CNRS UMR6226 Rennes F-3500 France., Doucet H; Univ. Rennes, CNRS UMR6226 Rennes F-3500 France., Soulé JF; Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences 75005 Paris France jean-francois.soule@chimieparistech.psl.eu. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2023 Aug 01; Vol. 14 (34), pp. 9055-9062. Date of Electronic Publication: 2023 Aug 01 (Print Publication: 2023). |
| DOI: | 10.1039/d3sc02992a |
| Abstrakt: | We introduce a versatile Rh(i)-catalyzed cascade reaction, combining C(sp 2 )-H bond functionalization and amidation between N -arylphosphanamines and acrylates. This innovative approach enables the rapid synthesis of dihydroquinolinone scaffolds, a common heterocycle found in various pharmaceuticals. Notably, the presence of the phosphorus atom facilitates the aniline ortho -C(sp 2 )-H bond activation prior to N-P bond hydrolysis, streamlining one-pot intramolecular amidation. Moreover, we demonstrate the applicability of this reaction by synthesizing an antipsychotic drug. Detailed mechanistic investigations revealed the involvement of a Rh-H intermediate, with substrate inhibition through catalyst saturation. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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