New Monoorganostannanes as Efficient Reagents for Palladium-Catalyzed Coupling Reactions

Acid‐Catalyzed Conversion of 7‐Ethynyl‐ and 7‐Vinylcyclohepta‐1,3,5‐trienes to Substituted Benzene Derivatives

“…The NMR spectroscopic data are in agreement with previously reported data. [32] C. Rearrangement of 1c in THF/TFA: Heating of compound 1c (31.5 mg) in THF/TFA (5:1, v/v) at 60°C for 24 h gave a yellow oil, which was shown to be a mixture of 7 and 8 (93.4:6.6 molar ratio) by 1 H NMR spectroscopy. The mixture was separated by GPC to afford 7 (28.0 mg, 89%) and 8 (2.0 mg, 6%).…”

CC Bond‐Forming Reactions

“…Progression in a coupling cycle would further require OH -, CO 3 2-, or F -, not present under the used Stille coupling conditions [178,179]. The Stille conditions proved very useful for affording many aryl-aryl [1,4,180,181,182], vinyl-aryl [9,161,183,184] and also alkyl-aryl [185] compounds bearing hydrolytically labile moieties. The commonly used reactivities of aryl or vinyl halide components are like those in the Scheme 9 Stille coupling: R and R' are aromatic or vinylic residues.…”

“…Monoalkyl or monoaryl halo bis hexamethyldisilazanylstannanes have also been shown to be useful precursors for aryl-aryl, vinyl-aryl, allyl-aryl, and even alkyl-aryl coupling reactions. Apart from their broad scope as coupling precursors, they allow facile extraction of water-soluble Sn species from the hydrophobic coupling products [185].…”

Synthesis of 7-Vinylflavone and 7-Aminoflavone by Palladium-Catalyzed Coupling Reactions

“…When the reacflavones are difficult to obtain. We attempted to synthesize tion was carried out under StilleЈs conditions [30] (Entry 1), flavones aminated at ring A by palladium-catalyzed amin-some black material appeared in the reaction mixture after ation, which would be a practical complementary method about 2.5 h, possibly due to decomposition of the catalyst. for synthesizing aminoflavone.…”