Phenolate anion-catalyzed direct activation of inert alkyl chlorides driven by visible light,Organic Chemistry Frontiers

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Phenolate anion-catalyzed direct activation of inert alkyl chlorides driven by visible light
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-09-17 , DOI: 10.1039/d1qo01128f
Delian Wei ₁ , Xipan Li ₁ , Lei Shen ₁ , Yuzhen Ding ₁ , Kangjiang Liang ₁ , Chengfeng Xia ₁

Affiliation

Alkyl chlorides are abundant and stable chemical feedstocks, but their chemical inertness hinders their widespread availability as reactants in synthetic chemistry. In this study, we demonstrate an efficient photochemical strategy to activate inert C(sp³)–Cl bonds catalyzed by phenolate anion photocatalysts. Mechanistic studies indicate that the cleavage of unactivated C(sp³)–Cl bonds is mediated by a direct SET process from photo-excited phenolate anions. This strategy conveniently engages a diverse range of unactivated primary, secondary, and tertiary alkyl chlorides in radical C–O bond formation, dehalogenation, and cyclization under mild conditions.

中文翻译：

苯酚阴离子催化可见光驱动的惰性烷基氯化物的直接活化

烷基氯是丰富且稳定的化学原料，但它们的化学惰性阻碍了它们在合成化学中作为反应物的广泛应用。在这项研究中，我们展示了一种有效的光化学策略来激活由苯酚阴离子光催化剂催化的惰性 C(sp ³ )-Cl 键。机理研究表明，未活化的 C(sp ³ )-Cl 键的断裂是由光激发的酚盐阴离子的直接 SET 过程介导的。该策略可以方便地在温和条件下使各种未活化的伯、仲和叔烷基氯参与自由基 C-O 键的形成、脱卤和环化。

更新日期：2021-09-28

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