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Published on: May 21, 2019
Method and Mechanistic Insights to 1,2-Aminochlorinate Alkenes using Blue-Light Activated Dichlorocarbamates
Sini Irvankoski1, Michael T Davenport2, Daniel H Ess2
1Department of Chemistry and Materials Science, Aalto University, 00076, Espoo, Finland.
Abstract:
Blue light activation of N,N-dichlorocarbamates facilitates a direct 1,2-aminochlorination of unactivated olefins to yield 1,2-chloro-N-Cl compounds under ambient conditions. Mechanistic studies suggest that N,N-dichlorocarbamates undergo a photochemical excitation to yield a neutral nitrogen-centered radical, which rapidly reacts with olefins in an anti-Markovnikov fashion. Using this method, a range of functionally diverse substrates are successfully aminochlorinated to yield the corresponding 1,2-chloro-N-Cl compounds.
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