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Interception of Cobalt‐Based Carbene Radicals with α‐Aminoalkyl Radicals: A Tandem Reaction for the Construction of β‐Ester‐γ‐amino Ketones
Author(s) -
Zhang Jie,
Jiang Jiewen,
Xu Dongmei,
Luo Qiang,
Wang Hongxiang,
Chen Jijun,
Li Huihuang,
Wang Yaxiong,
Wan Xiaobing
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408874
Subject(s) - radical , carbene , chemistry , chemoselectivity , cobalt , substrate (aquarium) , photochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , oceanography , geology
The interception of cobalt‐based carbene radicals with α‐aminoalkyl radicals was combined with the Kornblum–DeLaMare reaction and provides β‐ester‐γ‐amino ketones, which are otherwise difficult to obtain in high chemoselectivity. Mechanistically, this transformation is an interplay of cobalt‐based carbene radicals, organoradicals, and ionic intermediates and involves the construction of two CC bonds and one CO bond in a one‐pot process. The reaction also features a wide substrate scope and is highly efficient and insensitive to moisture and air.