Dagar, Neha; Singh, Swati; Raha Roy, Sudipta published the artcile< Synergistic Effect of Cerium in Dual Photoinduced Ligand-to-Metal Charge Transfer and Lewis Acid Catalysis: Diastereoselective Alkylation of Coumarins>, Application In Synthesis of 94-02-0, the main research area is carboxylic acid coumarin photoinduced decarboxylative alkylation cerium; alkylcoumarin diastereoselective preparation; cerium diastereoselective decarboxylative alkylation catalyst.
We report the dual role of cerium to promote the photoinduced ligand-to-metal charge transfer (LMCT) process for the generation of the alkyl radical and subsequent Lewis acid catalysis to construct stereodefined C-C bonds. This paradigm utilized ubiquitous carboxylic acids as alkyl radical surrogates and offers excellent diastereoselectivity for the formation of C-4 alkylated coumarins in good to excellent yield. UV-vis spectroscopy studies in combination with in situ Fourier transform IR spectroscopy are consistent with the proposed mechanism, supporting the participation of the CeIV-carboxylate complex in photoinduced LMCT and its subsequent homolysis to generate the alkyl radial through the exclusion of CO2. Finally, the oxophilicity of cerium enables a two-point complexation with the in situ generated enolate intermediate and facilitates the diastereoselective protonation to form the desired product. Furthermore, this mild and atom-economical catalytic manifolds allow the late-stage modification of pharmaceuticals.
Journal of Organic Chemistry published new progress about Carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Application In Synthesis of 94-02-0.
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