Substituent Electronic Effects Govern Direct Intramolecular C–N Cyclization of <i>N</i>-(Biphenyl)pyridin-2-amines Induced by Hypervalent Iodine(III) Reagents
作者:Jean-Ho Chu、Wen-Ting Hsu、Yi-Hua Wu、Meng-Fan Chiang、Nan-Hai Hsu、Hao-Ping Huang、Ming-Jung Wu
DOI:10.1021/jo501822m
日期:2014.12.5
The hypervalent iodine(III) reagent-induced the direct intramolecular C–N cyclization of N-(biphenyl)pyridin-2-amines to 6-arylbenzimidazoles and N-pyridinyl-9H-carbazoles is presented. The substituent electronic effects governing the formation of benzimidazoles and carbazoles from the reaction of N-(biphenyl)pyridin-2-amines with hypervalent iodine(III) reagents is investigated. Radical trapping and
提出了高价碘(III)试剂诱导的N-(联苯基)吡啶-2-胺直接分子内C–N环化为6-芳基苯并咪唑和N-吡啶基-9 H-咔唑的方法。研究了N-(联苯基)吡啶-2-胺与高价碘(III)试剂反应时支配苯并咪唑和咔唑形成的取代基电子效应。进行了自由基捕获和紫外可见光谱检测阳离子自由基的实验。提出了这些反应的合理机制。还介绍了基于取代基电子效应的N-(联苯)乙酰胺的选择性分子内C–N和C–O环化。