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 language | English |
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Pages (from-to) | 3186-3193 |
Number of pages | 8 |
Journal | Advanced Synthesis and Catalysis |
Volume | 359 |
Issue number | 18 |
DOIs | |
State | Published - Sep 18 2017 |
Keywords
- 6-endo-dig oxo-cyclization
- dimerization
- silver catalysis
- spiro-1H-isochromenes
- trimerization