Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2–SO2R coupling†,Chemical Science

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Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2–SO2R coupling†
Chemical Science ( IF 7.6 ) Pub Date : 2018-02-22 00:00:00 , DOI: 10.1039/c7sc05402e
María Jesús Cabrera-Afonso ₁ , Zhi-Peng Lu ₁ , Christopher B Kelly ₁ , Simon B Lang ₁ , Ryan Dykstra ₂ , Osvaldo Gutierrez ₂ , Gary A Molander ₁

Affiliation

This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis. Using aryl sulfinate salts, the C–S bond can be forged at room temperature under base-free conditions. An array of aryl- and heteroaryl halides are compatible with this approach. The broad tolerance and mild nature of the described reaction could potentially be employed to prepare sulfones with biological relevance (e.g., in bioconjugation, drug substance synthesis, etc.) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for C_sp³–C_sp² cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with experimental and computational data is presented.

中文翻译：

通过 Ni/光氧化还原双重催化作用接合亚磺酸盐，可实现轻松的 Csp2–SO2R 偶联†

该报告详细介绍了通过镍/光氧化还原双重催化构建芳基和杂芳基砜的策略的开发和实施。使用芳基亚磺酸盐，可以在室温、无碱条件下形成C-S键。一系列芳基卤化物和杂芳基卤化物与该方法兼容。所描述的反应的广泛耐受性和温和性质可以潜在地用于制备具有生物相关性的砜（例如，在生物共轭、药物物质合成等中），如在药物样化合物或其前体的合成中所证明的。当与现有的用于 C _{sp ³} –C _{sp ²}交叉偶联的 Ni/光氧化还原化学配对时，可以很容易地从双功能亲电子试剂组装一系列不同的砜支架。提出了与实验和计算数据一致的机械流形。

更新日期：2018-02-22

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