Umpolung by N‐Heterocyclic Carbenes: Generation and Reactivity of the Elusive 2,2‐Diamino Enols (Breslow Intermediates) | Zendy

Berkessel Albrecht | Zendy; Elfert Silvia | Zendy; Yatham V. Reddy | Zendy; Neudörfl JörgM. | Zendy; Schlörer Nils E. | Zendy; Teles J. Henrique | Zendy

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Umpolung by N‐Heterocyclic Carbenes: Generation and Reactivity of the Elusive 2,2‐Diamino Enols (Breslow Intermediates)

Author(s) -

Berkessel Albrecht,

Elfert Silvia,

Yatham V. Reddy,

Neudörfl JörgM.,

Schlörer Nils E.,

Teles J. Henrique

Publication year - 2012

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201205878

Subject(s) - umpolung , carbene , deprotonation , chemistry , benzoin , aldehyde , reactivity (psychology) , alkene , organic chemistry , catalysis , nucleophile , medicine , ion , alternative medicine , pathology

54 years later : Saturated imidazolidin‐2‐ylidenes react with aldehydes to smoothly produce the elusive 2,2‐diamino enols A (“Breslow intermediates”, first postulated in 1958) of carbene‐catalyzed umpolung reactions. The 2,2‐diamino enols A react with additional aldehyde in a cross‐benzoin reaction. The methylated Breslow intermediates B are accessible by deprotonation of methoxymethyl azolium salts.

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