Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand,The Journal of Organic Chemistry

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Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-14 00:00:00 , DOI: 10.1021/acs.joc.8b00197
Taemoon Song ₁ , Ji Eun Park ₁ , Young Keun Chung ₁

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The [Rh(COD)Cl]₂/xantphos/Cs₂CO₃ system efficiently catalyzes the reductive N-alkylation of aryl nitro compounds with alcohols by a borrowing-hydrogen strategy to afford the corresponding imine products in good to excellent yields. In the absence of xantphos, the [Rh(COD)Cl]₂/Cs₂CO₃ catalytic system behaves as an effective catalyst for the dehydrogenative coupling of alcohols to esters, with nitrobenzene as a hydrogen acceptor. The reactivity of the rhodium catalytic system can be easily manipulated to selectively afford the imine or ester.

中文翻译：

铑催化的苄醇和硝基芳烃合成亚胺和酯：取决于是否存在膦配体，催化剂反应性的变化

[Rh（COD）Cl] ₂ / xantphos / Cs ₂ CO ₃系统通过借位氢策略有效催化芳基硝基化合物与醇的还原性N-烷基化，从而以良好或优异的收率提供相应的亚胺产品。在不存在黄药的情况下，[Rh（COD）Cl] ₂ / Cs ₂ CO ₃催化体系可作为醇与酯脱氢偶联的有效催化剂，硝基苯为氢受体。铑催化体系的反应性可以很容易地控制以选择性地提供亚胺或酯。

更新日期：2018-03-14

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