Direct Access to S-Heterocycles by Scandium(III) Triflate Catalyzed Cyclization of Aromatic Thiols and Diols

A simple and environmentally friendly method to prepare S-heterocycles by cyclization of aromatic thiols and diols with H2O as a byproduct is described. The Sc(OTf)(3)-catalyzed dehydrative cyclizations of aromatic thiols and diols provided the corresponding thiopyran and thiophene derivatives. Cont...

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Bibliographic Details
Published inSynlett Vol. 32; no. 18; pp. 1869 - 1873
Main Authors Minakawa, Maki, Minami, Keisuke, Sato, Yuya
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 11.11.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
diols
CASCADE REACTIONS
SULFIDES
C-S bond formation
C-S
BOND FORMATION
S-heterocycles
ALKYNES
cyclization
HYDROTHIOLATION
scandium triflate
ALCOHOLS
thiols
ALLYLIC SUBSTITUTION
EFFICIENT
TOOLS
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Summary:A simple and environmentally friendly method to prepare S-heterocycles by cyclization of aromatic thiols and diols with H2O as a byproduct is described. The Sc(OTf)(3)-catalyzed dehydrative cyclizations of aromatic thiols and diols provided the corresponding thiopyran and thiophene derivatives. Control experiments were also performed to obtain insights into the reaction pathway
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1720350