Metal catalysis has a dominant role in modern organic
chemistry. In particular, cross-coupling reactions allow bond
formations, which have previously been impossible to perform.[
1] Precious metal catalysts dominate the field, but
alternative systems based on nickel and copper salts have
also, historically, been important. In particular, recent systems
based on these metals have been described that provide
products in a highly efficient manner.[2]
In this context, one of us (C.B.) reported iron-catalyzed
cross-couplings leading to arylated amides, phenols, thiols,
and alkynes.[3, 4] Commonly, 10 mol% of an iron salt in
combination with 20 mol% of a ligand (a diamine or a
diketone) in a solvent such as toluene at 1358C (using closed
vials) was used. It was noticed by chemists at RWTH Aachen
and MIT (past and present) that the catalyst activity
depended on the metal salt purity and even more so on its
commercial source.[5] Also, a parallel between the results with
the iron systems and some of those realized with copper
catalysts by S.L.B.s group and that of Song was recognized.
For example, as in the case of much of the chemistry from
S.L.B.s group, N,N’-dimethyl-1,2-diamines were superior
ligands, and the best results were realized in conversions of
aryl iodides.
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