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Updated: Oct 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Symmetric and non-symmetric anthracen-diyl bis(alkylidynes)
Benjamin J Frogley1, Anthony F Hill1, Steven S Welsh1
1Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory, ACT 2601, Australia. a.hill@anu.edu.au.
Abstract:
Three examples of 9-bromo-10-(alkylidynyl)anthracenes, [W{CC(C6H4)2CBr}(CO)2(L)] (L = hydrotris(dimethylpyrazol-1-yl)borate Tp*, hydrotris(pyrazol-1-yl)borate Tp, hydrotris(2-mercapto-N-methylimidazol-1-yl)borate Tm) were prepared via modified Fischer-Mayr acyl oxide-abstraction protocols. With a sufficiently bulky ancillary ligand (L = Tp*) the aryl bromide is ammenable to cross-coupling reactions that enable more elaborate derivatives to be prepared. These including symmetric bis(alkylidynyl)anthracenes as well as non-palindromic examples bearing disparate metals and/or co-ligands. In contrast, these couplings fail for smaller ligands (L = Tp, Tm) where it was found that Pd0 or Pt0 were instead able to coordinate across two WC bonds to give trimetallic bow-tie complexes, [W2M{μ-CC(C6H4)2CBr}2(CO)4(L)2] (M = Pd, Pt; L = Tp, Tm).
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