480424-70-2Relevant articles and documents
Visible- And UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts
Kubosaki, Suzuka,Takeuchi, Haruka,Iwata, Yutaka,Tanaka, Yosuke,Osaka, Kazuyuki,Yamawaki, Mugen,Morita, Toshio,Yoshimi, Yasuharu
, p. 5362 - 5369 (2020/05/19)
Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only our two-molecule organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.
Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?
Chen, Xiao-Yue,Huang, Yu-Hao,Zhou, Jian,Wang, Peng
, p. 1269 - 1272 (2020/08/13)
Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.
Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation
Liu, Chengwei,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
supporting information, p. 16721 - 16726 (2018/11/30)
Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.