Activation of α-diazocarbonyls by organic catalysts: diazo group acting as a strong N-terminal electrophile

Angewandte Chemie
Lei LiYu-Long Zhao

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.

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Citations

Jul 28, 2016·Chemical Reviews·Steven W M CrossleyRyan A Shenvi
Sep 9, 2016·The Journal of Organic Chemistry·Kostiantyn O MarichevMichael P Doyle
Mar 24, 2017·Chemistry : a European Journal·Kenneth Virgel N Esguerra, Jean-Philip Lumb
Apr 29, 2016·Chemical Communications : Chem Comm·Gao-Feng ZhaCheng-Pan Zhang
Sep 4, 2019·Organic & Biomolecular Chemistry·Xin WangKai Sun

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