Norbornene Derivatives-Controlled Palladium-Catalyzed Divergent Synthesis of Dibenzo[a,c]cycloheptenones and Fluorenones from Aryl Iodides and α-Oxocarboxylic Acids,Organic Letters

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Norbornene Derivatives-Controlled Palladium-Catalyzed Divergent Synthesis of Dibenzo[a,c]cycloheptenones and Fluorenones from Aryl Iodides and α-Oxocarboxylic Acids
Organic Letters ( IF 4.9 ) Pub Date : 2024-01-18 , DOI: 10.1021/acs.orglett.3c04065
Liwei Zhou ₁ , Pengyang Jing ₂ , Zhiwei Li ₂ , Rui Liu ₂ , Jiannan Chen ₁ , Guobo Deng ₂ , Yun Liang ₂ , Yuan Yang ₂

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A palladium-catalyzed divergent cascade decarboxylative annulation of aryl iodides and α-oxocarboxylic acids using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, fluorenones are synthesized with moderate to excellent yields via a Catellani reaction that involves sequential ortho-C–H arylation and ipso-decarboxylative acylation of aryl iodides. Employing oxanorbornadiene (ONBD) instead of NBE enables the assembly of dibenzo[a,c]cycloheptenones by a retro-Diels–Alder reaction rather than the release of an ONBD. Additionally, the synthetic utility of this method is demonstrated by the diversification of the products.

中文翻译：

降冰片烯衍生物控制的钯催化从芳基碘化物和 α-氧代羧酸发散合成二苯并[a,c]环庚烯酮和芴酮

据报道，使用降冰片烯（NBE）衍生物作为受控开关，钯催化芳基碘化物和α-氧代羧酸的发散级联脱羧成环。当 NBE 用作介体时，通过 Catellani 反应以中等至优异的产率合成芴酮，该反应涉及芳基碘化物的连续邻位-C–H 芳基化和本身脱羧酰化。使用氧杂降冰片二烯 (ONBD) 代替 NBE 可以通过逆狄尔斯-阿尔德反应组装二苯并[ a , c ]环庚烯酮，而不是释放 ONBD。此外，该方法的合成效用通过产品的多样化得到证明。

更新日期：2024-01-18

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