Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes,Advanced Synthesis & Catalysis

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Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-07-19 , DOI: 10.1002/adsc.202100555
Fei Zhao ₁ , Jing Chen ₂ , Jin Qiao ₁ , Yangbin Lu ₁ , Xiaoning Zhang ₁ , Hui Mao ₃ , Shiyao Lu ₁ , Xin Gong ₁ , Siyu Liu ₁ , Xiaowei Wu ₄ , Long Dai ₁

Affiliation

Alkynes generally serve as C₂ synthons in transition-metal-catalyzed C−H annulations, herein, exploiting electron-deficient alkynes as unconventional C₁ synthons, the chemo- and regiospecific synthesis of functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a redox-neutral rhodium(III)-catalyzed [4+1] annulation of N-carbamoyl indoles has been achieved. This process is characterized by high chemo- and regioselectivity, broad substrate scope, good tolerance of functional groups, moderate to high yields and mild redox-neutral conditions, thus affording a robust approach to access valuable 1H-imidazo[1,5-a]indol-3(2H)-ones.

中文翻译：

通过氧化还原中性铑 (III)-催化的吲哚和炔烃之间的 [4+1] 环化反应化学和区域选择性合成功能化 1H-咪唑并 [1,5-a] 吲哚-3(2H)-酮

炔烃通常在过渡金属催化的 C−H 环化中用作 C ₂合成子，在此，利用缺电子炔烃作为非常规 C ₁合成子，功能化 1 H-咪唑并[1,5- a ]的化学和区域特异性合成indol-3(2 H )-ones 通过氧化还原中性铑 (III) 催化的 [4+1] 环化N-氨基甲酰基吲哚已经实现。该工艺的特点是化学选择性和区域选择性高、底物范围广、官能团耐受性好、产率中等至高和氧化还原中性条件温和，从而为获取有价值的 1 H-咪唑并[1,5- a ]indol-3(2 H）-那些。

更新日期：2021-09-21

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