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

Chemical Communications : Chem Comm
Ming HuJin-Heng Li

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.

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Citations

Jun 27, 2017·Organic & Biomolecular Chemistry·Jin-Tao YuJiang Cheng
Aug 7, 2019·Organic & Biomolecular Chemistry·Le-Han GaoWen-Ting Wei
Aug 14, 2021·Chemical Reviews·Xue-Qiang ChuChao-Jun Li

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