Activation of α‐Diazocarbonyls by Organic Catalysts: Diazo Group Acting as a Strong N‐Terminal Electrophile. (28th August 2015)

• Record Type: Journal Article
• Authors: Li, Lei; Chen, Jia‐Jia; Li, Yi‐Jin; Bu, Xiu‐Bin; Liu, Qun; Zhao, Yu‐Long
• Is Part Of: Angewandte Chemie. Volume 127:Number 41(2015)
• Page Start: 12275
• Page End: 12279
• Publication Date: 2015-08-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201505064
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>