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Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones
Nature Catalysis ( IF 37.8 ) Pub Date : 2021-08-02 , DOI: 10.1038/s41929-021-00661-7
Xukai Zhou 1 , Yan Xu 1, 2 , Guangbin Dong 1
Affiliation  

Arene- and heteroarene-fused rings are pervasive in biologically active molecules. Direct annulation between a C–H bond on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C–H annulation with diverse aromatic rings. Here, we show a deacylative annulation strategy for preparing a large variety of aromatic-fused rings from linear simple ketone precursors. The reaction starts with homolytic cleavage of the ketone α C–C bond via a pre-aromatic intermediate, followed by a radical-mediated dehydrogenative cyclization. Using widely available ketones as the robust radical precursors, this deconstructive approach allows streamlined assembly of complex polycyclic structures with broad functional group tolerance.



中文翻译:

通过未应变酮的 C-C 裂解脱酰化辅助 C-H 烷基化环化

芳烃和杂芳烃稠合环普遍存在于生物活性分子中。芳香核心上的 C-H 键和连接的烷基部分之间的直接环化提供了一种直接接近这些支架的方法;然而,这种策略通常会因需要特殊的反应基团和/或不太相容的环化条件而受到阻碍。如果可以使用一个共同的天然官能团作为手柄来实现具有不同芳香环的通用 C-H 环化,那将具有综合吸引力。在这里,我们展示了一种脱酰基环化策略,用于从线性简单酮前体制备多种芳族稠环。该反应首先通过前芳族中间体均裂酮α C-C 键,然后是自由基介导的脱氢环化。

更新日期:2021-08-02
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