Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 31, Pages 4417-4422Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100569
Keywords
Heterogeneous catalysis; Mesoporous silica; Nucleophilic substitution; Oxovanadium; Thioethers
Categories
Funding
- JSPS KAKENHI [18H02556, 20 K22542]
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED [21am0101084]
- Analytical Instrumentation Facility, Graduate School of Engineering, Osaka University
- Grants-in-Aid for Scientific Research [18H02556] Funding Source: KAKEN
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The direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica-supported oxovanadium catalyst (VMPS4). The VMPS4 catalyst exhibited excellent chemoselectivity towards alcohols and could be easily recycled through simple centrifugation.
Direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica-supported oxovanadium catalyst (VMPS4). Benzyl and allyl alcohols were compatible in this reaction under mild conditions, affording the products in high yields. The VMPS4 catalyst showed excellent chemoselectivity toward alcohols in the presence of acid-labile functional groups, which is in contrast to that observed for the commonly used Lewis acid catalysts, which exhibit poor selectivity. The VMPS4 catalyst could be recycled by simple centrifugation, and the catalytic activity was maintained over seven cycles.
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