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Activation of α‐Diazocarbonyls by Organic Catalysts: Diazo Group Acting as a Strong N‐Terminal Electrophile
Author(s) -
Li Lei,
Chen JiaJia,
Li YiJin,
Bu XiuBin,
Liu Qun,
Zhao YuLong
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505064
Subject(s) - electrophile , diazo , chemistry , methylene , nucleophile , catalysis , amidine , bicyclic molecule , medicinal chemistry , terminal (telecommunication) , combinatorial chemistry , organic chemistry , telecommunications , computer science
For the first time α‐diazocarbonyls have been used as highly active N‐terminal electrophiles in the presence of bicyclic amidine catalysts. The CN bond‐forming reactions of active methylene compounds as C nucleophiles with α‐diazocarbonyls as N‐terminal electrophiles proceed quickly under ambient conditions, in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), because of the formation of the reactive N‐terminal electrophilic intermediates. DBU activates both the active methylene and α‐diazocarbonyl. Importantly, this reaction is general for both active methylenes and α‐diazocarbonyls, and the activation mode will lead to new synthetic applications of α‐diazocarbonyls.