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Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

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Abstract

A Lewis acid-catalyzed one-pot aza-Michael addition/fragmentation/sulfinyl conjugate addition/cyclization cascade of o-QMs and arylsulfonyl hydrazides is described for the first time. This technology engages a broad range of substrates with both components under mild conditions, giving the corresponding valuable 3-sulfonylbenzofurans in generally good yields. These investigations show the use of arylsulfonyl hydrazides as nucleophiles for the first time in catalytic C–N and C–S bond formation with o-QMs.

Graphical abstract: Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

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Publication details

The article was received on 29 Sep 2019, accepted on 24 Oct 2019 and first published on 25 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01196J
Org. Chem. Front., 2019, Advance Article

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    Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

    F. Meng, R. Wang, H. Huang, S. Gong, Q. Li, S. Zhang, C. Ma, C. Li and J. Du, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01196J

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