Asymmetric Induction in the Electrochemical Cross-Coupling of Aryl Halides with α-Chloropropionic Acid Derivatives Catalyzed by Nickel Complexes

Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions

“…Nickel-catalyzed electroreductive coupling reactions have been pursued as an alternative to methods using heterogeneous metal powders [103]. The electrocatalytic coupling of a-chloroesters with aryl halides produces chiral a-arylamides using chiral auxiliaries [104] and an asymmetric reductive coupling of vinyl bromides and secondary alkyl chlorides affords excellent enantioselectivity [105].…”

Nickel/Photoredox‐Catalyzed Asymmetric Reductive Cross‐Coupling of Racemic α‐Chloro Esters with Aryl Iodides

“…In summary,wehave developed the first enantioselective dual nickel and organic photoredox catalyzed reductive crosscoupling between a-chloro esters and aryl iodides to afford aaryl esters.E nantioenriched a-aryl ester derivatives are important precursors to nonsteroidal anti-inflammatory medications.Key features and advantages of this method include broad scope in both coupling partners,a voidance of preformed organometallic reagents,a nd circumvention of stoichiometric metal reductants used in most cross-electrophile coupling reactions.F uture directions include the use of electrochemical methods as as ource of electrons for enantioselective reductive coupling reactions. [24]…”

Nickel/Photoredox‐Catalyzed Asymmetric Reductive Cross‐Coupling of Racemic α‐Chloro Esters with Aryl Iodides

“…Key features and advantages of this method include broad scope in both coupling partners, avoidance of preformed organometallic reagents, and circumvention of stoichiometric metal reductants used in most cross‐electrophile coupling reactions. Future directions include the use of electrochemical methods as a source of electrons for enantioselective reductive coupling reactions …”