Photocatalytic Strategy for Decyanative Transformations Enabled by Amine-Ligated Boryl Radical

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-10 DOI:10.1021/acs.orglett.4c04701

Yuto Yoshida, Waka Okada, Kazutake Takada, Shuichi Nakamura, Naoki Yasukawa

引用次数: 0

Abstract

Decyanation after α-functionalization by exploiting the inherent properties of cyano groups enables the strategic assembly of a carbon scaffold. Herein, we demonstrate an amine-ligated boryl radical-mediated cyano group transfer (CGT) strategy of malononitriles under photocatalytic conditions. This strategy allows for the cleavage of C(sp³)–CN and the formation of C(sp³)–D and C(sp³) to realize decyanative deuteration and cyclization via radical-polar crossover. Computational studies successfully demonstrated the reactivity of CGT promoters can be accurately assessed.

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氨基连接硼基自由基脱氰转化的光催化策略

利用氰基的固有性质，在α-功能化后进行脱氰，使碳支架的战略性组装成为可能。在此，我们证明了在光催化条件下丙二腈氨基连接硼基自由基介导的氰基转移（CGT）策略。该策略允许C(sp3) -CN裂解，形成C(sp3) -D和C(sp3)，通过自由基-极性交叉实现脱氰氘化和环化。计算研究成功地证明了CGT启动子的反应性可以被准确地评估。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.