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S. Luo et al.
Letter
Synlett
potential application of this protocol was showcased by the
synthesis of a series of key deuterated building blocks for
the construction of benzylic position deuterated drugs and
agrochemicals. More broadly, the method represents the
first reductive deuteration of benzylic-type O-ketyl radicals
using mild and highly chemoselective lanthanide(II) re-
agents. Further studies on the reactivity of ketyl-type radi-
cals will be forthcoming.
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Funding Information
We thank the National Key Research and Development Plan of China
(2017YFD0200504), the National Natural Science Foundation of China
(NSFC; 11801558), the Natural Science Foundation of Beijing Munici-
pality (2192026), and Tianjin Haiyi Tech. Ltd. for financial support.NationKRaleyseanDrchdev
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Supporting Information
Supporting information for this article is available online at
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C.; Weakley, T. J. R.; Tyler, D. R. J. Am. Chem. Soc. 2000, 122, 9427.
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(d) Bai, W.; Lee, K.-H.; Tse, S. K. S.; Chan, K. W.; Lin, Z.; Jia, G.
Organometallics 2015, 34, 3686.
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References and Notes
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(20) Typical Procedure for the Preparation of Model Compound
(4-Heptylphenyl)methan-d2-ol (2a)
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To a solution of samarium(II) iodide (0.10 M in THF; 12 mL, 1.2
mmol, 6.0 equiv) a solution of methyl 4-heptylbenzoate (46.9
mg, 0.200 mmol) in THF (2.0 mL) was added, followed by Et3N
(0.33 mL, 2.4 mmol) and D2O (0.261 mL, 14.4 mmol) under Ar at
room temperature and stirred vigorously. After 15 min, the
excess of SmI2 was oxidized by bubbling air through the reac-
tion mixture. The reaction mixture was diluted with CH2Cl2 (10
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