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Chemically Non‐Innocent Cyclic (Alkyl)(Amino)Carbenes: Ligand Rearrangement, C−H and C−F Bond Activation
Author(s) -
Turner Zoë R.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602264
Subject(s) - carbene , intramolecular force , chemistry , ligand (biochemistry) , alkyl , intermolecular force , hexafluorobenzene , catalysis , stereochemistry , medicinal chemistry , molecule , organic chemistry , receptor , biochemistry
Abstract A cyclic (alkyl)(amino)carbene (CAAC) was found to undergo unprecedented rearrangements and transformations of its core structure in the presence of Group 1 and 2 metals. Although the carbene was also found to be prone to intramolecular C−H activation, it was competent for intermolecular activation of a variety of sp‐, sp 2 ‐, and sp 3 ‐hybridized C−H bonds. Double C−F activation of hexafluorobenzene was also observed in this work. These processes all hold relevance to the role of these carbenes in catalysis, as well as to their use in the synthesis of new and unusual main group or transition metal complexes.