Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D₂O as Deuterium Source

Shihui Luo, Chaoqun Weng, Yuxuan Ding, Chen Ling, Michal Szostak, Xiaodong Ma*, Jie An*

*College of Science, China Agricultural University, Beijing 100083; Department of Nutrition and Health, China Agricultural University, Beijing 100193, China, Email: maxiaodongcau.edu.cn, jie_ancau.edu.cn

S. Luo, C. Weng, Y. Ding, C. Ling, M. Szostak, X. Ma, J. An, Synlett, 2021, 32, 51-56.

DOI: 10.1055/s-0040-1705944

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Abstract

The use of D₂O and SmI₂ as a mild single-electron donor enables a general single-electron transfer reductive deuteration of readily commercially available aromatic esters for the synthesis of α,α-dideuterio benzyl alcohols. This operationally convenient method features high deuterium incorporations and very good functional group tolerance.

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Pentafluorophenyl Esters: Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI₂ and D₂O as a Deuterium Source

H. Li, Y. Hou, C. Liu, Z. Lai, L. Ning, R. Szostak, M. Szostak, J. An, Org. Lett., 2020, 22, 1249-1253.

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Key Words

reductive deuteration, α,α-dideuterio benzyl alcohol, samarium diiodide, single-electron transfer, reduction of esters, D₂O

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ID: J72-Y2021