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Issue 37, 2018
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Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H2O2 promoted tandem oxidative annulation and 1,2-sulfur migration

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Abstract

A novel TBAI-catalyzed tandem thio-Michael addition/oxidative annulation of allenes and thioamides for the construction of polysubstituted 2-arylthiophenes under a sulfur migration transformation protocol has been developed. The transition-metal-free protocol achieves the oxidative cyclization reaction of thioamides containing electron-rich substituents with allenes to construct polysubstituted thiophenes selectively by controlling oxidation conditions.

Graphical abstract: Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H2O2 promoted tandem oxidative annulation and 1,2-sulfur migration

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Supplementary files

Article information


Submitted
30 Jul 2018
Accepted
02 Sep 2018
First published
03 Sep 2018

Org. Biomol. Chem., 2018,16, 8253-8257
Article type
Communication

Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H2O2 promoted tandem oxidative annulation and 1,2-sulfur migration

T. Han and X. Luo, Org. Biomol. Chem., 2018, 16, 8253
DOI: 10.1039/C8OB01835A

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