Tunable Dimerization and Trimerization of β-Alkynyl Ketones via Silver Catalysis for Accessing Spiro and Dispiro Compounds Containing 1H-Isochromene

Dan Wang, Shuai Liu, Xin Chan Lan, Armando Paniagua, Wen Juan Hao, Guigen Li, Shu Jiang Tu, Bo Jiang

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

New silver-catalyzed tunable dimerization and trimerization reactions of β-alkynyl ketones have been established, enabling multiple C−C bond-forming events to selectively access skeletally diverse spiroisochromenes with generally good yields. The silver-enabled bicycloaddition of β-alkynyl ketones with water offered hydroxylated spiroisochromenes. Without water, spiroisochromenes with a methylene moiety were obtained through catalytic 6-endo-dig oxo-cyclization/[4+2] cycloaddition cascades by using pyridine as additive whereas employment of 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (BiNPO4H) as a Brønsted acid catalyst rendered the unprecedented dispiro trimerization products through double C(sp3)–H functionalization. (Figure presented.).

Original languageEnglish
Pages (from-to)3186-3193
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number18
DOIs
StatePublished - Sep 18 2017

Keywords

  • 6-endo-dig oxo-cyclization
  • dimerization
  • silver catalysis
  • spiro-1H-isochromenes
  • trimerization

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