148562-11-2Relevant academic research and scientific papers
Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids
Hinkes, Stefan P.A.,Klein, Christian D.P.
supporting information, p. 3048 - 3052 (2019/05/10)
Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.
Potassium haloalkyltrifluoroborate salts: Synthesis, application, and reversible ligand replacement with MIDA
Burke, Sarah J.,Gamrat, James M.,Santhouse, Jacqueline R.,Tomares, Dylan T.,Tomsho, John W.
, p. 5500 - 5503 (2015/09/21)
Increased interest in boron-containing pharmaceuticals has created a need for efficient syntheses of organoboron compounds. This article describes one- and two-pot syntheses of potassium haloalkyltrifluoroborate salts, important building blocks for the incorporation of boron into complex molecules. The sequential, high-yielding procedures (65% to 92%) involve hydroboration of commercially available haloalkenes with dichloroborane (prepared in situ from triethylsilane and boron trichloride), followed by treatment of the crude hydroboration products with potassium hydrogen difluoride. A hexaethyldisiloxane byproduct that hinders the isolation of the desired boronic acids and esters was identified and easily removed via this procedure. The value of the potassium haloalkyltrifluoroborate salts is subsequently demonstrated in example substitution reactions, which were followed by a reversible ligand replacement with N-methyliminodiacetic acid (MIDA). Reversibly switching these orthogonal boron protecting groups enables full exploitation of their favorable chemical properties, effectively bridging these platforms and further expanding their scope and utility.
