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N-Heterocyclic Carbene Catalysis Exploiting Oxidative Imine Umpolung for the Generation of Imidoyl Azoliums
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.joc.0c00360 Tamal Kanti Das 1, 2 , Krishnaprasad Madica 3 , Jagadeesh Krishnan 3 , Udaya Kiran Marelli 1, 2 , Akkattu T. Biju 3
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.joc.0c00360 Tamal Kanti Das 1, 2 , Krishnaprasad Madica 3 , Jagadeesh Krishnan 3 , Udaya Kiran Marelli 1, 2 , Akkattu T. Biju 3
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Although NHC-catalyzed umpolung of imines are known, the related reactions under oxidative conditions are limited. Described herein is the two-step process involving the initial formation of aldimines from the corresponding aldehydes and 2-amino benzyl alcohols followed by NHC-catalyzed cyclization proceeding via the imidoyl azoliums under oxidative conditions. The reaction allowed the synthesis of trifluoromethylated 3,1-benzoxazines in good yields and broad scope. The role of NHC in the intramolecular cyclization and preliminary mechanistic experiments are also provided.
中文翻译：
N-杂环卡宾催化利用氧化亚胺Umpolung生成亚胺基偶氮
尽管已知NHC催化的亚胺类脂蛋白，但在氧化条件下的相关反应受到限制。本文描述了两步过程，该过程包括从相应的醛和2-氨基苄醇初步形成醛亚胺，然后在氧化条件下经由亚氨基偶氮鎓进行NHC催化的环化。该反应使三氟甲基化的3，1-苯并恶嗪的合成具有良好的收率和广泛的范围。还提供了NHC在分子内环化和初步机理实验中的作用。
更新日期：2020-03-21
中文翻译：
N-杂环卡宾催化利用氧化亚胺Umpolung生成亚胺基偶氮
尽管已知NHC催化的亚胺类脂蛋白，但在氧化条件下的相关反应受到限制。本文描述了两步过程，该过程包括从相应的醛和2-氨基苄醇初步形成醛亚胺，然后在氧化条件下经由亚氨基偶氮鎓进行NHC催化的环化。该反应使三氟甲基化的3，1-苯并恶嗪的合成具有良好的收率和广泛的范围。还提供了NHC在分子内环化和初步机理实验中的作用。
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