锌介导的β-硼基NHPI酯的断裂使1,2-硼自由基转移合成宝石-二氟烯基硼酸盐。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-14 DOI:10.1021/acs.orglett.5c01486

Wei-Jun Pang,Xiao-Chen Wang,Jing Sun,Xue-Song Li,Ming-Dong Zhou

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引用次数: 0

摘要

硼迁移是有机合成中一类重要而有趣的反应。本文提出了一种通过锌介导β-硼基NHPI酯的1,2-硼自由基转移合成宝石-二氟烯基硼酸盐的新方法。这些β-硼基烷基自由基随后经历1,2-硼转移，产生有价值的烷基自由基，这些烷基自由基可以进一步被α-三氟甲基烯烃捕获，以构建各种宝石-二氟烷基硼酸盐，包括药物分子。此外，这种交叉偶联过程可用于重要分子支架的后期修饰，以构建结构复杂的有机分子。

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Zn-Mediated Fragmentation of β-Boryl NHPI Esters Enabling the Radical 1,2-Boron Shift for the Synthesis of gem-Difluoroalkenyl Boronates.

Boron migration is a type of vital and intriguing reaction in organic synthesis. Herein, a new approach for the synthesis of gem-difluoroalkenyl boronates via the Zn-mediated 1,2-boron radical shift of β-boryl NHPI esters is developed. These β-boryl alkyl radicals subsequently undergo a 1,2-boron shift to produce valuable alkyl radical species, which can be further trapped by α-trifluoromethyl alkenes to construct a diverse array of gem-difluoroalkenyl boronates, including pharmaceutical molecules. Moreover, this type of cross-coupling process can be used for late-stage modification of important molecular scaffolds to build intricately structured organic molecules.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.