Generally, the acidity of carbon-hydrogen bonds is most sensitive to functionality just one or two bonds away. Here, we present an approach to the formation of carbon-carbon σ bonds by remote proton elimination, a distinct mode of carbon-hydrogen activation enabled by distal acidification through five carbon-carbon bonds. Application of remote proton elimination to cyclodecyl cations unveiled an appealing method for the synthesis of decalins. The transformation is regioconvergent, proceeds without the need for a directing group or precious metal, and demonstrates exquisite site selectivity. An in-depth computational study illuminated the reaction mechanism. Additionally, we describe the complete stereoisomeric enrichment of the decalin products through epimerization mediated by hydrogen atom transfer.

中文翻译：

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远程质子消除：通过远端酸化实现 C-H 激活


一般来说，碳-氢键的酸性对仅一两个键之外的官能团最敏感。在这里，我们提出了一种通过远程质子消除形成碳-碳σ键的方法，这是一种通过五个碳-碳键的远端酸化实现的碳-氢活化的独特模式。将远程质子消除应用于环癸基阳离子揭示了一种有吸引力的十氢化萘合成方法。该转化是区域收敛的，无需导向基团或贵金属即可进行，并且表现出精致的位点选择性。深入的计算研究阐明了反应机理。此外，我们描述了通过氢原子转移介导的差向异构化十氢萘产物的完整立体异构富集。