1264616-18-3Relevant academic research and scientific papers
A robust three-step telescoped synthesis of electron-deficient amide substituted arylboronic acids
Zhu, Jason,Razler, Thomas M.,Xu, Zhongmin,Conlon, David A.,Sortore, Eric W.,Fritz, Alan W.,Demerzhan, Roman,Sweeney, Jason T.
scheme or table, p. 438 - 442 (2012/02/03)
A robust three-step telescoped process for the preparation of electron-deficient amide-substituted arylboronic acids from readily available bromobenzoic acids has been developed. An EDC-HOBT-promoted amide formation of a bromobenzoic acid was followed by subjection of the product stream to a palladium-mediated cross-coupling with B2(pin)2. The resultant mixture of the arylboronate ester and arylboronic acid was directly treated with NaIO4, followed by a heptane-MeTHF crystallization, to cleanly afford the corresponding arylboronic acid in good yield. This general procedure was used to synthesize electron-deficient amide-substituted arylboronic acids with a diverse array of electron-withdrawing substituents.
