Mn-Mediated Radical Cascade Cyclization of 1,6-Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones,Advanced Synthesis & Catalysis

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Mn-Mediated Radical Cascade Cyclization of 1,6-Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-30 , DOI: 10.1002/adsc.202201054
Chada Raji Reddy ₁ , Roshan Chandrakant Kajare ₁ , Punna Nagender ₂

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Herein, we report the synthesis of functionalized dihydro-benzo[b]fluorenones through a manganese-mediated cascade radical cyclization of β-alkynyl propenones [1,6-enynes] with arylboronic acids. In the present strategy, the in-situ generated aryl radical undergoes chemo-selective addition followed by 5-exo-trig cyclization. The reaction is emphasized by high atom- and step-economy with the construction of three new C−C bonds to access the dihydrobenzo[b]fluorenones in 68–81% yield under mild reaction conditions. The synthetic efficacy of the developed method is evidenced by the construction of new C−C and C−N bonds.

中文翻译：

锰介导的 1,6-烯炔与芳基硼酸的自由基级联环化得到二氢苯并 [b] 芴酮

在此，我们报道了通过锰介导的β-炔基丙烯酮 [1,6-烯炔] 与芳基硼酸的级联自由基环化反应，合成了功能化二氢苯并 [ b ] 芴酮。在本策略中，原位生成的芳基自由基经过化学选择性加成，然后进行 5 -exo-trig环化。该反应强调了高原子经济性和步骤经济性，通过构建三个新的 C-C 键，在温和的反应条件下以 68-81% 的产率获得二氢苯并 [ b ] 芴酮。新 C−C 和 C−N 键的构建证明了所开发方法的合成功效。

更新日期：2022-11-30

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