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. 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

Takaoki Koyanagi  1 , Ananda Herath  1 , Ashley Chong  1 , Maxim Ratnikov  1 , Andrew Valiere  1 , Jim Chang  1 , Valentina Molteni  1 , Jon Loren  1
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One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2-Sp3 Cross-Coupling

Takaoki Koyanagi et al. Org Lett. .

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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