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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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Publication details

The article was received on 30 Jul 2018, accepted on 02 Sep 2018 and first published on 03 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB01835A
Citation: Org. Biomol. Chem., 2018, Advance Article
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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

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

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