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

Kim Joseph T. | Zendy; Kel'in Alexander V. | Zendy; Gevorgyan Vladimir | Zendy

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

Author(s) -

Kim Joseph T.,

Kel'in Alexander V.,

Gevorgyan Vladimir

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200390064

Subject(s) - cycloisomerization , thio , chemistry , group (periodic table) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis

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.

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