Safety of Methyl 3-phenylpropionate. In 2020.0 ACS CATAL published article about POSITRON-EMISSION-TOMOGRAPHY; CARBOXYLIC-ACIDS; MERGING PHOTOREDOX; H BONDS; FLUORINE; NICKEL; DEOXYFLUORINATION; CARBOFLUORINATION; CATALYSIS; DERIVATIVES in [Wang, Hongyu; Liu, Chen-Fei; Ho, Yee Ann; Koh, Ming Joo] Natl Univ Singapore, Dept Chem, Singapore 117549, Singapore; [Song, Zhihui; Yuan, Mingbin; Gutierrez, Osvaldo] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA in 2020.0, Cited 86.0. The Name is Methyl 3-phenylpropionate. Through research, I have a further understanding and discovery of 103-25-3.
Fluorine-containing organic molecules, particularly those that bear (sp(3))C-F bonds, are rapidly gaining prominence in modern chemical synthesis. Although extensive studies have been devoted to the preparation of secondary and tertiary fluorides, crucial shortcomings remain: for example, lengthy substrate synthesis, contrived installation of difficult-to-remove directing/activating units, excessive waste generation and/or limited functional group compatibility. Here, we show that readily accessible alpha-onofluoro carboxylic acids, which are conventionally difficult substrates for cross-coupling, undergo direct decarboxylative crosscoupling with sp(2-) and sp(3-)hybridized organohalides to afford a wide assortment of fluorinated products. Reactions are typically promoted by a combination of 1 mol % of an Ir-based photocatalyst and 2-15 mol % of a bipyridine-Ni complex, delivering products in up to 86% yield under blue LED light irradiation. Concise synthesis of key therapeutic candidates underscores utility, complementarity, and distinct advantages compared with existing methods. DFT calculations are used to rationalize the distinct reactivity of alpha-fluoro carboxylic acid substrates (vs nonfluorinated parent acids) under decarboxylation conditions.
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Patent; SANOFI; US2011/294788; (2011); A1;,
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