Robust, scalable construction of an electrophilic deuterated methylthiolating reagent: facile access to SCD3-containing scaffolds

We have established a practical and concise method for the straightforward access of a universal deuterated methylthiolating reagent through a one-pot gram-scale operation under mild conditions. This odourless electrophilic SCD3 reagent was widely applied to react with numerous representative nucleo...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 18; pp. 3015 - 3018
Main Authors Xiao, Xiao, Huang, Yin-Qiu, Tian, Hong-Yu, Bai, Jun, Cheng, Fei, Wang, Xu, Ke, Miao-Lin, Chen, Fen-Er
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.03.2022
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Deuteration
Deuterium
Lewis acids
Lewis bases
Nucleophiles
Physical Sciences
Reagents
Science & Technology
DRUG
HYDROGEN ISOTOPE
METHYLATION
PATHWAY
CHEMISTRY
DISCOVERY
DEUTERIUM
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Summary:We have established a practical and concise method for the straightforward access of a universal deuterated methylthiolating reagent through a one-pot gram-scale operation under mild conditions. This odourless electrophilic SCD3 reagent was widely applied to react with numerous representative nucleophiles and approached various valuable SCD3 analogues with excellent levels of deuterium content (>99% D). The divergent further transformations were smoothly carried out to obtain the significant derivatives with different oxidative states in high efficiency.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d1cc07184j