50598-33-9Relevant articles and documents
Synthesis of Cyclic Anhydrides via Ligand-Enabled C–H Carbonylation of Simple Aliphatic Acids
Herron, Alastair N.,Yu, Jin-Quan,Zhuang, Zhe
supporting information, p. 16382 - 16387 (2021/06/23)
The development of C(sp3)–H functionalizations of free carboxylic acids has provided a wide range of versatile C?C and C?Y (Y=heteroatom) bond-forming reactions. Additionally, C–H functionalizations have lent themselves to the one-step preparation of a number of valuable synthetic motifs that are often difficult to prepare through conventional methods. Herein, we report a β- or γ-C(sp3)–H carbonylation of free carboxylic acids using Mo(CO)6 as a convenient solid CO source and enabled by a bidentate ligand, leading to convenient syntheses of cyclic anhydrides. Among these, the succinic anhydride products are versatile stepping stones for the mono-selective introduction of various functional groups at the β position of the parent acids by decarboxylative functionalizations, thus providing a divergent strategy to synthesize a myriad of carboxylic acids inaccessible by previous β-C–H activation reactions. The enantioselective carbonylation of free cyclopropanecarboxylic acids has also been achieved using a chiral bidentate thioether ligand.
SYNTHESIS OF 4,4- AND 5,5-DISUBSTITUTED 4,5-DIHYDRO-6H-CANTHIN-6-ONES
Hajicek, Josef,Holubek, Jiri,Trojanek, Jan
, p. 2749 - 2762 (2007/10/02)
The paper describes regiospecific synthesis of 4,4- and 5,5-disubstituted 4,5-dihydro-6H-canthin-6-ones III and XVIII, starting from half-esters of 2,3-disubstituted succinic acids, V and XIV.The formation of the anomalous 5,5-disubstituted canthin-4,6-diones XVII is ascribed to oxidation of the intermediate XIX.The 1H NMR spectra of the compounds prepared are discussed.
