Direct electrocarboxylation of various -acylimines with atmospheric CO is achieved in an undivided cell under mild conditions, affording substituted α-amino acids in yields of 62-95%. This reaction is conducted with high efficiency using triethanolamine as an external reductant under nonsacrificial anode conditions, and can be facilely performed on gram scale. Preliminary mechanistic studies including cyclic voltammetry and control experiments support -radical carbanion as the key intermediate.
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http://dx.doi.org/10.1021/acs.orglett.2c01267 | DOI Listing |
Org Lett
May 2022
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, PR China.
Direct electrocarboxylation of various -acylimines with atmospheric CO is achieved in an undivided cell under mild conditions, affording substituted α-amino acids in yields of 62-95%. This reaction is conducted with high efficiency using triethanolamine as an external reductant under nonsacrificial anode conditions, and can be facilely performed on gram scale. Preliminary mechanistic studies including cyclic voltammetry and control experiments support -radical carbanion as the key intermediate.
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