Photochemical Carboborylation and Three-component Difunctionalization of α,β-unsaturated Ketones with Boronic Acids via Tosylhydrazones

IF 7.6 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Chemical Science Pub Date : 2024-11-06 DOI:10.1039/d4sc06537a
Alvaro Valdés-Maqueda, Manuel Plaza, Carlos Valdes
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Abstract

The reactions of cyclic α,β-unsaturated N-tosylhydrazones and alkylboronic acids promoted by 370-390 nm light in the presence of a base give rise to allylic boronic acids that can be trapped as the corresponding pinacolboronates by treatment with pinacol. This reaction features wide scope regarding both coupling partners and functional group tolerance, allowing for the incorporation of a variety of natural product-derived fragments. The allylic boronic acids can be also reacted in a one-pot process with aldehydes, to produce homoallylic alcohols with very high diastereoselectivity. A three-component one-pot procedure has been developed revealing that the methodology is a powerful tool for the generation of structural diversity that is accomplished by incorporation of an ample variety of each of the three elements. Moreover, from a synthetic perspective, in the reaction, the formation of two C-C bonds, at the carbonyl and the β positions of a α,β-unsaturated carbonyl, has been achieved in the three-component reaction.
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α、β-不饱和酮与硼酸通过对甲苯磺酰基肼发生光化学羰基化和三组分双官能化反应
环状 α、β-不饱和 N-对甲基苯磺酰肼和烷基硼酸在 370-390 纳米波长的光照和碱的作用下发生反应,生成烯丙基硼酸,经频哪醇处理后可生成相应的频哪醇硼酸酯。该反应在偶联剂和官能团耐受性方面都有广泛的应用范围,可以加入各种天然产物衍生的片段。烯丙基硼酸还可以与醛进行单锅反应,生成具有极高非对映选择性的均烯丙基醇。我们已经开发出一种三组份一锅法,揭示了该方法是一种强大的工具,可以通过加入这三种元素中的每一种来实现结构多样性。此外,从合成的角度来看,在三组份反应中,α,β-不饱和羰基的羰基和 β 位置上形成了两个 C-C 键。
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来源期刊
Chemical Science
Chemical Science CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
14.40
自引率
4.80%
发文量
1352
审稿时长
2.1 months
期刊介绍: Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.
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