344-03-6Relevant articles and documents
Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
, p. 3860 - 3865 (2018/04/26)
Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
Organothallium Compounds. XVIII The Effect of Antimony Pentafluoride and Fluorosulfuric Acid on the Thallation of Polyfluoroarenes
Deacon, Glen B.,Smith, Richard N.M.
, p. 1587 - 1597 (2007/10/02)
The polyfluoroarenes m-H2C6F4, m-O2NC6F4H, m- and p-BrC6F4H, (p-HC6F4)2, C6F5H, 1,3,5-F3C6H3 and m-FSO2C6F4H have been thallated by thallic trifluoroacetate in fluorosulfuric acid in the presence of antimony pentafluoride.Substantial dithallation of m-H2C6F4 and 1,3,5-F3C6H3 and slight trithallation of the latter have been achieved.The products were identified by conversion into the corresponding polyfluoroiodoarenes on reaction with aqueous sodium iodide.From the reaction with pentafluorobenzene, pentafluorophenylthallium(III) species have been characterized. 1,2,4,5-Tetrafluoro-3-methoxybenzene was thallated by thallic trifluoroacetate in 1,2-dichloroethane in the presence of boron trifluoride etherate, but C6F5H and p-MeC6F4H failed to react.