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Transition-Metal-Mediated Cleavage of C-C Bonds in Aromatic Rings
Martin Jakoobi1, Alexey G Sergeev1
1Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, United Kingdom.
Abstract:
Metal-mediated cleavage of aromatic C-C bonds has a range of potential synthetic applications: from direct coal liquefaction to synthesis of natural products. However, in contrast to the activation of aromatic C-H bonds, which has already been widely studied and exploited in diverse set of functionalization reactions, cleavage of aromatic C-C bonds remains Terra incognita. This Minireview summarizes the recent progress in this field and outlines key challenges to be overcome to develop synthetic methods based on this fundamental organometallic transformation.
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Bonding in Metals
Properties of Transition Metals
Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
Phase Transitions
Cleavage and Blastulation