Rhodium(i)-catalyzed cascade C(sp(2))-H bond alkylation - amidation of anilines: phosphorus as traceless directing group - Archive ouverte HAL Access content directly
Journal Articles Chemical Science Year : 2023

Rhodium(i)-catalyzed cascade C(sp(2))-H bond alkylation - amidation of anilines: phosphorus as traceless directing group

Abstract

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.
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Dates and versions

hal-04193415 , version 1 (01-09-2023)

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Attribution - NonCommercial

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Marie Peng, Denis Ari, Thierry Roisnel, Henri Doucet, Jean-Francois Soule. Rhodium(i)-catalyzed cascade C(sp(2))-H bond alkylation - amidation of anilines: phosphorus as traceless directing group. Chemical Science, 2023, 14, pp.9055-9062. ⟨10.1039/d3sc02992a⟩. ⟨hal-04193415⟩
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