N‐Heterocyclic Carbenes: Organocatalysts with Moderate Nucleophilicity but Extraordinarily High Lewis Basicity | Zendy

Maji Biplab | Zendy; Breugst Martin | Zendy; Mayr Herbert | Zendy

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N‐Heterocyclic Carbenes: Organocatalysts with Moderate Nucleophilicity but Extraordinarily High Lewis Basicity

Author(s) -

Maji Biplab,

Breugst Martin,

Mayr Herbert

Publication year - 2011

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.201102435

Subject(s) - nucleophile , electrophile , carbene , chemistry , pyridine , organocatalysis , lewis acids and bases , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis

Unique organocatalysts : Arduengo's carbenes 1 and 2 are 10 3 times more nucleophilic than the Enders carbene 3 , which attacks electrophiles with similar rates as diazabicyclo[5.4.0]undecene (DBU) and 4‐(dimethylamino)pyridine (DMAP). The unique organocatalytic activities of 1 – 3 are explained by their extraordinarily high Lewis basicities, which exceed those of PPh 3 , DBU, and DMAP by more than 100 kJ mol −1 .

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