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DOI: 10.1055/s-0030-1258759
Synthesis of 2,3-Disubstituted Indoles by Iron(II)-Catalyzed Aromatic C-H Amination
S. Jana, M. D. Clements, B. K. Sharp, N. Zheng*
University of Arkansas, Fayetteville, USA
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
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Significance
Reported is a general synthesis of 2,3-disubstituted indoles 2 via a ring opening of aryl 2H-azirines 1 catalyzed by FeCl2. Based on previous results (K. Isomura, K. Uto, H. Taniguchi J. Chem. Soc., Chem. Commun. 1977, 664; S. Chiba, G. Hattoti, K. Narasaka Chem. Lett. 2007, 36, 52), the 2H-azirine 1 is converted into indole 2 via a proposed vinyl nitrene intermediate. After screening several iron sources, the best results were obtained using FeCl2. Amides, aryl (substituted by EWGs and EDGs) halides, OTBS and CF3 substituents are tolerated in the reaction. Moreover, the annulation tolerates various aryl and alkyl C2- and C3-substituents in the 2H-azirine 1. The apparent single limitation is the requirement of a R¹ substituent. Finally, a plausible mechanism involving an iron nitrene complex was proposed.