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Method and Mechanistic Insights to 1,2‐Aminochlorinate Alkenes using Blue‐Light Activated Dichlorocarbamates

2025/03/12 by Sini Irvankoski, Michael T. Davenport, Daniel H. Ess +1 · 1 voice
Pharmacology, Toxicology and Pharmaceutics · Chemistry · #Fluorine in Organic Chemistry #Vanadium and Halogenation Chemistry

paper · pdf · doi:10.1002/chem.202403215

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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