- Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones
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Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.
- Huang, Chia-Yu,Li, Chao-Jun,Li, Jianbin,Qiu, Zihang,Wang, Haining
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supporting information
p. 13011 - 13020
(2020/09/01)
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- 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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- Method for synthesizing aryl three fluoro potassium borate method
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The invention discloses a novel method for synthesizing potassium aryl trifluoroborate. The novel method comprises the following steps: enabling backflow reaction of tetra(pyrrolidine) diboron in excessive alcohol or water to obtain tetra(alkoxy) diboron, and adding a potassium bifluoride water solution so as to obtain potassium trifluoroborate diboron acid, wherein a boronizing agent is white crystalline solid, is stable in air and moisture and is suitable for being stored for a long time. The agent and aryl halide are adopted to be subjected to Suzuki coupling so as to obtain the potassium aryl trifluoroborate salt, the operation is simple and convenient, the yield is high, and corrosion to glass equipment and reaction kettles can be avoided.
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Paragraph 0026; 0027; 0028
(2017/04/25)
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- The solid-state structure of diboronic acid, B2(OH)4
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The crystal structure of diboronic acid contains molecules of B2(OH)4 hydrogen-bonded into two-dimensional sheets linked by B...O interactions.
- Baber, R. Angharad,Norman, Nicholas C.,Orpen, A. Guy,Rossi, Jean
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p. 773 - 775
(2007/10/03)
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