- Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids
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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.
- Hinkes, Stefan P.A.,Klein, Christian D.P.
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supporting information
p. 3048 - 3052
(2019/05/10)
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- Process for the preparation of aniline boronic acids and derivatives thereof
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Production of anilineboronic acid derivatives (I) comprises converting an aniline compound (II) to a doubly protected derivative (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester (IV) to give a protected anilineboronic acid ester (V), and deprotecting (V). Production of anilineboronic acid derivatives of formula (I) comprises converting an aniline compound of formula (II) to a doubly protected derivative of formula (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester of formula (IV) to give a protected anilineboronic acid ester of formula (V), and deprotecting (V): [Image] PG : protecting group; R : H, halo, 1-20C alkyl or alkoxy, optionally substituted 6-12C aryl or aryloxy, heteroaryl or heteroaryloxy, optionally substituted 3-8C cycloalkyl, dialkylamino, diarylamino, alkylthio, arylthio, ester or acetal; X : H or halo; R1>-R3>H or optionally substituted 1-20C alkyl, or two of R1>-R3> can form a ring or another borate group.
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