Iodide-Catalyzed Reductions: Development of a Synthesis of Phenylacetic Acids

Abstract

A new convenient and scalable synthesis of phenylacetic acids has been developed via the iodide catalyzed reduction of mandelic acids. The procedure relies on in situ generation of hydroiodic acid from catalytic sodium iodide, employing phosphorus acid as the stoichiometric reductant.

Co-metabolic formation of substituted phenylacetic acids by styrene-degrading bacteria

“…They occur as natural ingredients in plants and fruits and are used as flavors and fragrances in cosmetics or food [14]. Additionally, these compounds have a high relevance for the pharmaceutical sector as precursors or drugs [29], [51]. For example, α-methylated phenylacetic acids are currently applied as starting materials for the production of virostatic agents [49] or for receptor agonists and antagonists, e.g.…”

“…Another important alternative is the carbonylation of benzyl chlorides in the presence of ruthenium(III) EDTA complexes [45], nickel catalysts [6], or rhodium-based catalysts [17]. Other chemical syntheses for compounds mentioned use α-hydroxynitriles [2], styrene and derivatives [8], or mandelic acid [29]. The α-methylated phenylacetic acids like ibuprofen are commonly obtained via corresponding phenylacetophenones from substituted- or non-substituted benzenes after initial Friedel–Crafts acylation [3], [12], [28], [43].…”

Production of a recombinant membrane protein in an Escherichia coli strain for the whole cell biosynthesis of phenylacetic acids

“…Both compounds are used for the synthesis of pharmaceuticals, insecticides, disinfectants, and products for the perfume industry [7], [8], [17], [18], [26], [38].…”

Microindolinone A, a Novel 4,5,6,7-Tetrahydroindole, from the Deep-Sea-Derived Actinomycete <em>Microbacterium </em>sp. MCCC 1A11207

“…Noteworthily, for the first time, the absolute configuration of such saturated indole was determined. By comparing the 1 H-, 13 C-NMR, MS, and OR data with those reported in the literature, 18 known compounds were identified as pyrrole-2-carboxylic acid (2) (12) [27], 5-methyluracil (13) [26], dibutyl phthalate (14) [28], 4-hydroxyphenylacetic acid (15) [29], [32], and (5-hydroxymethyl-furan-2-yl)-methanol (19) [33]. Surprisingly, these 19 compounds were all firstly isolated from Microbacterium species.…”