title: Activation of α-diazocarbonyls by organic catalysts: diazo group acting as a strong N-terminal electrophile.
abstract: For the first time α-diazocarbonyls have been used as highly active N-terminal electrophiles in the presence of bicyclic amidine catalysts. The CN 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.
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China).
authors: Lei
authors: L
authors: Li
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China).
authors: Jia-Jia
authors: JJ
authors: Chen
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China).
authors: Yi-Jin
authors: YJ
authors: Li
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China).
authors: Xiu-Bin
authors: XB
authors: Bu
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China). liuqun@nenu.edu.cn.
authors: Qun
authors: Q
authors: Liu
authors: Department of Chemistry, Northeast Normal University, Changchun, 130024 (P.R. China). zhaoyl351@nenu.edu.cn.
authors: Yu-Long
authors: YL
authors: Zhao
keywords: diazo compounds; heterocycles; organocatalysis; reaction mechanisms; synthetic methods