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

Hengzhao Li, Yuxia Hou, Chengwei Liu, Zemin Lai, Lei Ning, Roman Szostak, Michal Szostak* and Jie An*

*Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States; College of Science, China Agricultural University, Beijing 100193, China, Email: michal.szostakrutgers.edu, jie_ancau.edu.cn

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

DOI: 10.1021/acs.orglett.9b04383

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Abstract

The use of pentafluorophenyl esters as ketyl radical precursors, SmI₂ as a mild reducing agent, and D₂O as the deuterium source enables a highly chemoselective synthesis of α,α-dideuterio alcohols with exquisite incorporation of deuterium. This system tolerates a variety of functional groups.

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

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

Highly Chemoselective Reduction of Amides (Primary, Secondary, Tertiary) to Alcohols using SmI₂/Amine/H₂O under Mild Conditions

M. Szostak, M. Spain, A. J. Eberhard, D. J. Procter, J. Am. Chem. Soc., 2014, 136, 2268-2271.

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Key Words

reduction of esters, samarium diiodide

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ID: J54-Y2020