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Gold Difluorocarbenoid Complexes: Spectroscopic and Chemical Profiling
Author(s) -
Tskhovrebov Alexander G.,
Lingnau Julia B.,
Fürstner Alois
Publication year - 2019
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.201903957
Subject(s) - difluorocarbene , carbene , trifluoromethanesulfonate , chemistry , fluorine , ion , computational chemistry , photochemistry , medicinal chemistry , catalysis , organic chemistry
Gold carbenes of the general type [LAu=CR 2 ] + are sufficiently long‐lived for spectroscopic inspection only if the substituents compensate for the largely missing stabilization of the carbene center by the [LAu] + fragment. π‐Donation by two fluorine substituents (R=F) is insufficient; rather, difluorocarbene complexes are so deprived in electron density that they sequester even “weakly coordinating” anions such as triflate or triflimide. This particular bonding situation translates into unmistakable carbenium ion chemistry upon reaction with stilbene as a model substrate.