Divergent Reactions of α-Diazo 1,3-Dicarbonyl Compounds with Allylic Carbonates Involving Ketene versus Carbene Intermediates Enabled by Cooperative Rh(II)/Pd(0) Dual Catalysis,Organic Letters

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Divergent Reactions of α-Diazo 1,3-Dicarbonyl Compounds with Allylic Carbonates Involving Ketene versus Carbene Intermediates Enabled by Cooperative Rh(II)/Pd(0) Dual Catalysis
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-09 , DOI: 10.1021/acs.orglett.4c02947
De-Xin Song ₁ , Yu-Hua Song ₁ , Heng-Hua Huang ₁ , Xiao-Yan Huang ₁ , Fang Yang ₁ , Kegong Ji ₁ , Zi-Sheng Chen ₁

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A cooperative Rh(II)/Pd(0) dual-catalysis strategy that enabled divergent reactions of α-diazo 1,3-dicarbonyl compounds with allylic carbonates involving ketene versus carbene intermediates is described. The efficient synthesis of α-quaternary allylated β-keto-esters was accomplished by the Rh(II)/Pd(0) dual-catalysis allylic alkylation of α-diazo 1,3-dicarbonyl compounds. Alternatively, an unprecedented (1+4) annulation of α-diazo 1,3-dicarbonyl compounds with 2-(hydroxymethyl)allyl carbonates via Rh(II)/Pd(0) dual catalysis was also successfully developed, affording a wide variety of α-quaternary tetrahydrofurans in good to high yields.

中文翻译：

Rh(II)/Pd(0) 协同催化下 α-重氮 1,3-二羰基化合物与烯丙碳酸酯涉及乙烯酮与卡宾中间体的发散反应

描述了一种协同的 Rh(II)/Pd(0) 双催化策略，该策略能够实现 α-重氮 1,3-二羰基化合物与烯丙碳酸酯的不同反应，涉及烯酮与卡宾中间体。通过Rh(II)/Pd(0)双催化α-重氮1,3-二羰基化合物的烯丙基烷基化反应，实现了α-季烯丙基化β-酮酯的高效合成。另外，还成功开发了通过Rh(II)/Pd(0)双重催化作用的α-重氮1,3-二羰基化合物与2-(羟甲基)烯丙基碳酸酯的前所未有的(1+4)成环反应，提供了多种α-季四氢呋喃的收率良好至高。

更新日期：2024-09-09

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