ol8b04090_si_001.pdf (3.18 MB)
One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2–Sp3 Cross-Coupling
journal contribution
posted on 2019-01-23, 21:06 authored by Takaoki Koyanagi, Ananda Herath, Ashley Chong, Maxim Ratnikov, Andrew Valiere, Jim Chang, Valentina Molteni, Jon LorenA one-pot
electrochemical nickel-catalyzed decarboxylative sp2–sp3 cross-coupling reaction has been developed
using redox-active esters prepared in situ from alkyl carboxylates
and N-hydroxyphthalimide tetramethyluronium
hexafluorophosphate (PITU). This undivided cell one-pot
method enables C–C bond formation using inexpensive, benchtop-stable
reagents with isolated yields up to 95% with good functional
group tolerance, which includes nitrile, ketone, ester, alkene and
selectivity over other aromatic halogens.
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halogencross-couplingelectrochemicalalkene and selectivityDecarboxylativePITUketonedecarboxylativecell one-pot methodhydroxyphthalimide tetramethyluronium hexafluorophosphateNickel-Catalyzedbenchtop-stable reagentsSpnickel-catalyzedCross-Couplingformationredox-active estersOne-Potnitrilealkyl carboxylatesgoodgroup toleranceyieldElectrochemicalNbond
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