1,2-Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3-Thio-Substituted Furans and Pyrroles

The copper‐catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3‐thio‐substituted furans 3 a and pyrroles 3 b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mecha...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-01, Vol.42 (1), p.98-101
Main Authors: Kim, Joseph T., Kel'in, Alexander V., Gevorgyan, Vladimir
Format: Article
Language:English
Subjects:
Catalysis
Copper - chemistry
Cyclization
Furans - chemical synthesis
Furans - chemistry
heterocycles
homogeneous catalysis
Molecular Structure
Nitrogen - chemistry
nitrogen heterocycles
Pyrroles - chemical synthesis
Pyrroles - chemistry
Sulfhydryl Compounds - chemistry
Sulfides - chemistry
sulfur
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Summary:The copper‐catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3‐thio‐substituted furans 3 a and pyrroles 3 b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2‐migration of the thio group in the intermediate keto‐ and iminoallenyl sulfides 2. DMA=N,N‐dimethylacetamide.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200390064