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Photocatalytic deuterocarboxylation of alkynes with oxalate.

ABSTRACT: Herein, a catalytic photoredox-neutral strategy for alkyne deuterocarboxylation with tetrabutylammonium oxalate as the carbonyl source and D₂O as the deuteration agent was described. For the first time, the oxalic salt acted as both the reductant and carbonyl source through single electron transfer and subsequential homolysis of the C-C bond. The strongly reductive CO₂ radical anion species in situ generated from oxalate played significant roles in realizing the global deuterocarboxylation of terminal and internal alkynes to access various tetra- and tri-deuterated aryl propionic acids with high yields and deuteration ratios.

SUBMITTER: Xu P

PROVIDER: S-EPMC11323338 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Photocatalytic deuterocarboxylation of alkynes with oxalate.

Xu Pei P Jiang Hao-Qiang HQ Xu Hui H Wang Sai S Jiang Hui-Xian HX Zhu Song-Lei SL Yin Long L Guo Dong D Zhu Xu X

Chemical science 20240715 32

Herein, a catalytic photoredox-neutral strategy for alkyne deuterocarboxylation with tetrabutylammonium oxalate as the carbonyl source and D2O as the deuteration agent was described. For the first time, the oxalic salt acted as both the reductant and carbonyl source through single electron transfer and subsequential homolysis of the C-C bond. The strongly reductive CO2 radical anion species in situ generated from oxalate played significant roles in realizing the glob ...[more]

PMID: 39148785

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