Diverse ring opening of thietanes and other cyclic sulfides: an electrophilic aryne activation approach

Organosulfides are a common class of structure units in bioactive molecules and functional materials motivating continuous developments of efficient synthetic methods. Herein, we report an electrophilic aryne-activated ring opening protocol of one or two heteroatom containing saturated sulfur hetero...

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Published inChemical communications (Cambridge, England) Vol. 54; no. 11; pp. 1303 - 1306
Main Authors Zheng, Tianyu, Tan, Jiajing, Fan, Rong, Su, Shuaisong, Liu, Binbin, Tan, Chen, Xu, Kun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Continuity (mathematics)
Molecular structure
Nucleophiles
Physical Sciences
Ring opening
Science & Technology
STEVENS REARRANGEMENT
FACILE N-ARYLATION
TRIARYLSULFONIUM SALTS
MONOARYLATION
HETEROCYCLES
AMINES
EMPLOYING ARYNES
RATE CONSTANTS
CARBON-ATOM
NUCLEOPHILICITY
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Summary:Organosulfides are a common class of structure units in bioactive molecules and functional materials motivating continuous developments of efficient synthetic methods. Herein, we report an electrophilic aryne-activated ring opening protocol of one or two heteroatom containing saturated sulfur heterocycles. This three-component transformation proceeds under mild reaction conditions and displays exceptional generality of nucleophiles (C, O, S, N, and F centered nucleophiles), giving structurally diverse thioethers in good yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc08553b