Intermolecular cascade annulations of N-(arylsulfonyl)acrylamides with dual C(sp3)–H bonds: divergent access to indanes and pyrrolidin-2-ones. Issue 45 (15th May 2017)

• Record Type: Journal Article
• Authors: Hu, Ming; Guo, Ling-Yu; Han, Ying; Tan, Fang-Lin; Song, Ren-Jie; Li, Jin-Heng
• Is Part Of: Chemical communications. Volume 53:Issue 45(2017)
• Page Start: 6081
• Page End: 6084
• Publication Date: 2017-05-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc02608k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A new divergent cascade annulation reaction of N -(arylsulfonyl)acrylamides and dual alkyl C(sp 3 )–H bonds for selectively producing indanes and pyrrolidin-2-ones is presented. Abstract : A new divergent intermolecular cascade annulation reaction of N -(arylsulfonyl)acrylamides with dual alkyl C(sp 3 )–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.