Premium
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 .