A Ball-milling enabled zinc-mediated Barbier-type allylation reaction is reported. Notably runnning the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not require inert atmospheres or dry solvents and is reported on a range of aldehyde and ketone substrates, a gram scale process is demonstrated.Zn flake (325 mesh, 2.0 equiv.)DMSO (1.0 equiv.
We report a highly efficient ring-opening reaction of vinylcyclopropanes by boronic acids in water, using palladium nanoparticles formed from Pd(OAc)2 under ligandless conditions. Unsubstituted vinylcyclopropanes provide linear addition products with high selectivity, while a switch in regioselectivity to branched products is observed for aryl-substituted vinylcyclopropanes.
The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2' mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum substrates for this reaction, while electron-donating groups on the aromatic ring of the boronic acids resulted in moderate yields.
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