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Rhodium(i)-catalyzed cascade C(sp2)–H bond alkylation – amidation of anilines: phosphorus as traceless directing group† † Electronic supplementary information (ESI) available. CCDC 2252526. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc02992a

ABSTRACT: We introduce a versatile Rh(i)-catalyzed cascade reaction, combining C(sp2)–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(sp2)–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. A one-pot synthesis for dihydroquinolinones via Rh(i)-catalyzed C–H bond alkylation and amidation has been developed. The key roles of trivalent phosphorus and water were also identified through kinetic studies.

SUBMITTER: Peng M

PROVIDER: S-EPMC10466282 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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