Conjugate addition reactions of carbon nucleophiles to electron-deficient dienes

2010 ◽  
Vol 39 (11) ◽  
pp. 4080 ◽  
Author(s):  
Aurelio G. Csákÿ ◽  
Gabriela de la Herrán ◽  
M. Carmen Murcia
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Carbon Nucleophiles ◽  
Electron Deficient Dienes

ChemInform Abstract: Conjugate Addition Reactions of Carbon Nucleophiles to Electron-Deficient Dienes.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Aurelio G. Csaky ◽  
Gabriela de la Herran ◽  
M. Carmen Murcia
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Carbon Nucleophiles ◽  
Electron Deficient Dienes

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions

2018 ◽  
Vol 16 (3) ◽  
pp. 384-388 ◽  
Author(s):  
Gurdeep Singh ◽  
Prithwish Goswami ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Carbon Nucleophiles ◽  
Catalytic Application ◽  
Brønsted Base

The catalytic application of bis-(amino)cyclopropenylidene, as a non-covalent Brønsted base, in the 1,4- and 1,6-conjugate addition of carbon nucleophiles to enones andp-quinone methides, respectively, is described.

Diastereo-, Enantio-, and Z-Selective α,δ-Difunctionalization of Electron-Deficient Dienes Initiated by Rh-Catalyzed Conjugate Addition

2021 ◽  
Author(s):  
Christopher J. C. Cooze ◽  
Wesley McNutt ◽  
Markus D. Schoetz ◽  
Bohdan Sosunovych ◽  
Svetlana Grigoryan ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Electron Deficient Dienes
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