Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

Shape Selectivity in the Gold‐Catalyzed Hydration of Alkynes Using a Cavity‐Shaped Phosphine

“…NMR spectra, catalytic information and crystal structural determination. Additional references cited within the Supporting Information [19–23] …”

“…In addition, gold(III) complexes 5' and 7' showed full conversions for 1-hexyne and 3-hexyne, pointing out to the enhanced ability of gold(III) centres to mediate the hydration of both terminal and internal alkynes (Table 2, entries 13-16). [16] Finally, we compared the ability of the more proficient catalysts 4, 5 and 7 towards the hydration of diphenylacetylene and 4-octyne under the same conditions, which led to the formation of the corresponding ketones in 8-12 % and > 95 % yields (Table 2, entries [17][18][19][20][21][22], respectively, once in contrast to precatalyst 1, that revealed no activity even under more forcing conditions (ie. 1 mol%, after 24 h at 60 °C when using diphenylacetylene as substrate).…”

Regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers via siloxyallylpotassium intermediates

“…19 α-Oxygenated 1,4-diketone 7 was obtained in 89% yield via Rubottom oxidation. 20 Cu-catalyzed α-arylation of 3da was also accomplished using a diphenyliodonium salt, 21 giving 8 in 82% yield. Compound 8 could be further converted into the corresponding trisubstituted furan 9 and pyrrole 10 by a Paal–Knorr reaction.…”

One-pot synthesis of 3-functionalized (Z)-silyl enol ethers from 1-arylallylic alcohols by C,O-difunctionalization of dipotassio α,β-dianion intermediates

“…Silyl enol ethers are versatile synthetic precursors that can participate in various useful reactions. 1 In particular, 3-functionalized silyl enol ethers are valuable because they can be transformed into complex α,β-difunctionalized ketones by diverse α-functionalizations. 2 Therefore, general and efficient synthetic methods for these compounds are sought after.…”