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Issue 11, 2016
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Direct vicinal difunctionalization of alkynes through trifluoromethylation and aminosulfonylation via insertion of sulfur dioxide under catalyst-free conditions

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Abstract

Direct vicinal difunctionalization of alkynes through a catalyst-free four-component reaction of Togni's reagent, alkynes, sulfur dioxide, and hydrazines at room temperature is developed, which generates (E)-3,3,3-trifluoroprop-1-ene-1-sulfonohydrazides in good yields. This one-pot transformation works efficiently under extremely mild conditions without any catalysts and additives. The reaction process proceeds through trifluoromethylation of alkynes and aminosulfonylation via insertion of sulfur dioxide with excellent stereoselectivity and regioselectivity. Additionally, this reaction shows a broad substrate scope with good functional group tolerance. A plausible mechanism is proposed, supported by DFT calculations.

Graphical abstract: Direct vicinal difunctionalization of alkynes through trifluoromethylation and aminosulfonylation via insertion of sulfur dioxide under catalyst-free conditions

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Publication details

The article was received on 04 Aug 2016, accepted on 29 Aug 2016 and first published on 30 Aug 2016


Article type: Research Article
DOI: 10.1039/C6QO00434B
Citation: Org. Chem. Front., 2016,3, 1493-1497
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    Direct vicinal difunctionalization of alkynes through trifluoromethylation and aminosulfonylation via insertion of sulfur dioxide under catalyst-free conditions

    Y. Li, Y. Xiang, Z. Li and J. Wu, Org. Chem. Front., 2016, 3, 1493
    DOI: 10.1039/C6QO00434B

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