Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions,Israel Journal of Chemistry

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Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2020-03-12 , DOI: 10.1002/ijch.201900181
Anabel M. Rodríguez ₁ , Manuel R. Rodríguez ₁ , M. Mar Díaz‐Requejo ₁ , Pedro J. Pérez ₁

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The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by Tp^Br3Cu(NCMe) (Tp^Br3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles also verify the same transformation. The mechanism proposal is similar to that previously described for benzene amidation with the same catalyst and PhI=NTs, which takes place through aziridine formation, ring opening and 1,2‐hydrogen shift. A cascade reaction involving the coupling of 2,5‐dimethylfuran, 1,2,3‐trimethyl‐pyrrole and a nitrene NTs group is also described, leading to a 1,2‐dihydropyridine‐imine compound.

中文翻译：

铜催化的硝基转移反应对吡咯的官能化

据报道，通过引入亚硝基基团，吡咯具有催化功能。的C α -1H-吡咯的-H键时（TS =对甲苯磺酰基）基团由TP催化的NT的正式插入被酰胺化^BR3的Cu（NCMe）（TP ^BR3 =氢三（3,4,5-三溴吡唑基）硼酸）。N-取代的吡咯也证实了相同的转化。机理建议与先前描述的使用相同催化剂和PhI = NTs进行苯酰胺化的方法相似，该方法是通过形成氮丙啶，开环和1,2-氢转移来实现的。还描述了涉及2，5-二甲基呋喃，1,2,3-三甲基吡咯和亚硝基NTs基团偶联的级联反应，从而生成1,2-二氢吡啶-亚胺化合物。

更新日期：2020-03-12

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