Direct Aromatic Nitrosation Using 2-Methoxyethyl Nitrite as a NO Cation Source
Airu Hashidoko1, Taku Kitanosono1, Yasuhiro Yamashita1
1Department of Chemistry, School of Science, Graduate School of Science, The University of Tokyo, Tokyo 113-0033, Japan.
Abstract:
This work presents an acid-free method for aromatic nitrosation using 2-methoxyethyl nitrite (MOE-ONO). While originally developed as a NO radical source in our group, we demonstrate the utility of MOE-ONO as a NO cation source for aromatic electrophilic nitrosation. This method successfully nitrosates phenols, naphthols, and other pronucleophiles, completely suppressing undesired nitration by NO radicals. Notably, it enables nitrosation of acid-sensitive substrates, which has been difficult to achieve with existing protocols.
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