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Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2020-06-27 , DOI: 10.1021/jacs.0c03813
Jianbin Li 1 , Haining Wang 1 , Zihang Qiu 1 , Chia-Yu Huang 1 , Chao-Jun Li 1
Affiliation  

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, it also enables 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.

中文翻译:

醛和酮的无金属直接脱氧硼酰化

通过脱氧硼酸化将醛和酮直接转化为烷基硼酸酯是一种未知但非常理想的转化。在此,我们提出了一种在温和条件下进行羰基脱氧硼酰化的一步法和无金属方法。可以耐受多种芳香醛和酮,并成功转化为相应的苄基硼酸酯。通过与脂肪醛和酮相同的脱氧歧管,它还可以简明合成 1,1,2-三(硼酸酯),这是目前缺乏有效合成方法的化合物家族。鉴于其简单性和多功能性,我们预计这种新颖的硼酸化方法可以在有机硼合成中显示出巨大的前景,并在学术和工业环境中激发更多的羰基脱氧转化。
更新日期:2020-06-27
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