期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 34, 页码 10494-10501出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000581
关键词
allylic compounds; azides; C-H activation; microwave chemistry; porphyrinoids
资金
- Hong Kong Research Grants Council [HKU1/CRF/08, HKU700708]
- Areas of Excellence Scheme under the University Grants Committee of the Hong Kong Special Administrative Region, China [AoE/P-10/01]
[Fe-III(F-20-tpp)Cl] (F-20-tpp = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of alpha-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol% [Fe-III(F-20-tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16-fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion.
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