Abstract
AbstractEfforts to generate organomanganese reagents under ball‐milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre‐milling of the manganese is required.
Highlights
Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates
With regards to the generation of organometallic reagents, our group, as well as others, have explored the generation and use of organozinc species, whereby the reaction outcome is independent of the initial form of the zinc metal
Rather the reductive coupling of the arylidene malonate 2, leading to dimer 4 was instead isolated in 66 % yield
Summary
Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. Rather the reductive coupling of the arylidene malonate 2, leading to dimer 4 was instead isolated in 66 % yield.
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