Iron-Mediated Photochemical Anti-Markovnikov Hydroazidation of Unactivated Olefins
Henry Lindner1, Willi M Amberg1, Erick M Carreira1
1Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, ETH Zürich, 8093 Zurich, Switzerland.
Abstract:
Unactivated olefins are converted to alkyl azides with bench-stable NaN3 in the presence of FeCl3·6H2O under blue-light irradiation. The products are obtained with anti-Markovnikov selectivity, and the reaction can be performed under mild ambient conditions in the presence of air and moisture. The transformation displays broad functional group tolerance, which renders it suitable for functionalization of complex molecules. Mechanistic investigations are conducted to provide insight into the hydroazidation reaction and reveal the role of water from the iron hydrate as the H atom source.
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