628692-15-9Relevant articles and documents
Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s
Hafner, Andreas,Meisenbach, Mark,Sedelmeier, Joerg
supporting information, p. 3630 - 3633 (2016/08/16)
The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.
Efficient hydrolysis of organotrifluoroborates via silica gel and water
Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.
supporting information; experimental part, p. 7364 - 7369 (2010/01/16)
(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.