Copper(II)‐catalyzed Domino Reaction of the Acyclic Ketene‐(S,S)‐Acetals with Diazo Compounds: Convenient Synthesis of Poly‐substituted Thiophenes

Copper(II)‐catalyzed domino reaction between the acyclic ketene‐(S,S)‐acetals and diazo compounds has been successfully developed. This reaction proceeds through a sequential formation of electrophilic copper carbenoid, sulfur ylide and subsequent C−S bond coupling and cleavage. Notably, the domino...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-12, Vol.361 (24), p.5684-5689
Main Authors: Sun, Ran, Du, Yang, Tian, Cui, Li, Lei, Wang, He, Zhao, Yu‐Long
Format: Article
Language:English
Subjects:
Acetals
Acyclic ketene-(S,S)-acetals
Cascade chemical reactions
Copper
Copper catalyst
Copper compounds
Diazo compounds
Domino reaction
Poly-substituted thiophenes
Substitutes
Thiophenes
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Summary:Copper(II)‐catalyzed domino reaction between the acyclic ketene‐(S,S)‐acetals and diazo compounds has been successfully developed. This reaction proceeds through a sequential formation of electrophilic copper carbenoid, sulfur ylide and subsequent C−S bond coupling and cleavage. Notably, the domino reaction features broad the readily available acyclic ketene‐(S,S)‐acetals scope and provides a new strategy for the synthesis of poly‐substituted thiophenes.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901089