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Org Lett. 2019 Feb 1;21(3):816-820. doi: 10.1021/acs.orglett.8b04090. Epub 2019 Jan 23.

One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2-Sp3 Cross-Coupling.

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1
Genomics Institute of the Novartis Research Foundation , 10675 John Jay Hopkins Drive , San Diego , California 92121 , United States.

Abstract

A 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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