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Superelectrophilic Amidine Dications: Dealkylation by Triflate Anion
Author(s) -
Kovacevic Luka S.,
Idziak Christopher,
Markevicius Augustinas,
Scullion Callum,
Corr Michael J.,
Kennedy Alan R.,
Tuttle Tell,
Murphy John A.
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.201202990
Subject(s) - trifluoromethanesulfonate , electrophile , alkylation , amidine , chemistry , formamides , computational chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
Superelectrophiles : Formamides were designed that when treated with triflic anhydride would be transformed into superelectrophilic amidine dications. These dications were so electrophilic that they underwent in situ dealkylation by the triflate anion (see scheme; Tf=trifluoromethanesulfonyl). DFT calculations were used to determine the mechanistic details of the dealkylation reaction.