Visible-light mediated catalytic asymmetric radical deuteration at non-benzylic positions

Qinglong Shi, Meichen Xu, Rui Chang, Devenderan Ramanathan, Beatriz Peñin, Ignacio Funes-Ardoiz () and Juntao Ye ()
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Qinglong Shi: Shanghai Jiao Tong University
Meichen Xu: Shanghai Jiao Tong University
Rui Chang: Shanghai Jiao Tong University
Devenderan Ramanathan: Shanghai Jiao Tong University
Beatriz Peñin: Universidad de La Rioja
Ignacio Funes-Ardoiz: Universidad de La Rioja
Juntao Ye: Shanghai Jiao Tong University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Site- and enantioselective incorporation of deuterium into organic compounds is of broad interest in organic synthesis, especially within the pharmaceutical industry. While catalytic approaches relying on two-electron reaction manifolds have allowed for stereoselective delivery of a formal deuteride (D–) or deuteron (D+) at benzylic positions, complementary strategies that make use of one-electron deuterium atom transfer and target non-benzylic positions remain elusive. Here we report a photochemical approach for asymmetric radical deuteration by utilizing readily available peptide- or sugar-derived thiols as the catalyst and inexpensive deuterium oxide as the deuterium source. This metal-free platform enables four types of deuterofunctionalization reactions of exocyclic olefins and allows deuteration at non-benzylic positions with high levels of enantioselectivity and deuterium incorporation. Computational studies reveal that attractive non-covalent interactions are responsible for stereocontrol. We anticipate that our findings will open up new avenues for asymmetric deuteration.

Date: 2022
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DOI: 10.1038/s41467-022-32238-8

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