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Intermolecular cascade annulations of N-(arylsulfonyl)acrylamides with dual C(sp3)–H bonds: divergent access to indanes and pyrrolidin-2-ones

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Abstract

A new divergent intermolecular cascade annulation reaction of N-(arylsulfonyl)acrylamides with dual alkyl C(sp3)–H bonds for producing two types of five-membered rings, indanes and pyrrolidin-2-ones, is described. By using cycloalkanes and common alkanes as a one-carbon unit, an intermolecular [4+1] cascade carboannulation of N-(arylsulfonyl)acrylamides was achieved via a sequence of three C–H bond functionalization/aryl migration/desulfonylation that enables the formation of three C–C bonds and one N–H bond. When the one-carbon unit was changed to cycloalkyl ethers, the alternative intermolecular [4+1] cascade heteroannulation reaction occurred and allowed the construction of two C–C bonds and one C–N bond through dual C–H bond functionalization, aryl migration and desulfonylation cascades.

Graphical abstract: Intermolecular cascade annulations of N-(arylsulfonyl)acrylamides with dual C(sp3)–H bonds: divergent access to indanes and pyrrolidin-2-ones

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Publication details

The article was received on 05 Apr 2017, accepted on 05 May 2017 and first published on 05 May 2017


Article type: Communication
DOI: 10.1039/C7CC02608K
Citation: Chem. Commun., 2017, Advance Article
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    Intermolecular cascade annulations of N-(arylsulfonyl)acrylamides with dual C(sp3)–H bonds: divergent access to indanes and pyrrolidin-2-ones

    M. Hu, L. Guo, Y. Han, F. Tan, R. Song and J. Li, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02608K

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