2017
DOI: 10.1016/j.jorganchem.2017.05.055
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RhCl(CO)(PPh 3 ) 2 catalyzed α-alkylation of ketones with alcohols

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Cited by 31 publications
(21 citation statements)
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“…4′-Methyl-α,β-dihydrochalcone (1a), white solid, mp 61–63 °C (lit. 24 61–63 °C); 1 H NMR (600 MHz, CDCl 3 ): δ 7.90–7.83 (2H, m, H-2′, H-6′, AA′BB′), 7.33–7.24 (6H, m, H-2, H-3, H-5, H-6, H-3′, H-5′), 7.24–7.19 (1H, m, H-4), 3.32–3.25 (2H, m, H-α), 3.11–3.02 (2H, m, H-β), 2.41 (3H, s, C-4′-C ); 13 C NMR (150 MHz, CDCl 3 ): δ 199.00 (C̲ O), 143.94 (C-4′), 141.52 (C-1), 134.51 (C-1′), 129.39 (C-2′, C-6′), 128.63 (C-3, C-5), 128.54 (C-2, C-6), 128.28 (C-3′, C-5′), 126.21 (C-4), 40.47 (C-α), 30.34 (C-β), 21.76 (C-4′-C̲H 3 ); HR ESI-MS m / z calculated for C 16 H 17 O [M + H] + 225.1274, found [M + H] + 225.1282.…”
Section: Resultsmentioning
confidence: 99%
“…4′-Methyl-α,β-dihydrochalcone (1a), white solid, mp 61–63 °C (lit. 24 61–63 °C); 1 H NMR (600 MHz, CDCl 3 ): δ 7.90–7.83 (2H, m, H-2′, H-6′, AA′BB′), 7.33–7.24 (6H, m, H-2, H-3, H-5, H-6, H-3′, H-5′), 7.24–7.19 (1H, m, H-4), 3.32–3.25 (2H, m, H-α), 3.11–3.02 (2H, m, H-β), 2.41 (3H, s, C-4′-C ); 13 C NMR (150 MHz, CDCl 3 ): δ 199.00 (C̲ O), 143.94 (C-4′), 141.52 (C-1), 134.51 (C-1′), 129.39 (C-2′, C-6′), 128.63 (C-3, C-5), 128.54 (C-2, C-6), 128.28 (C-3′, C-5′), 126.21 (C-4), 40.47 (C-α), 30.34 (C-β), 21.76 (C-4′-C̲H 3 ); HR ESI-MS m / z calculated for C 16 H 17 O [M + H] + 225.1274, found [M + H] + 225.1282.…”
Section: Resultsmentioning
confidence: 99%
“…However, neohesperidin dihydrochalcone is a non-cariogenic, intensive and hypocaloric sweetener permitted by the EU and the FDA as a food additive [8,9]. Chemical hydrogenation of a double bond usually requires reagents containing transition metals, e.g., ruthenium or iridium complex [10,11], which are relatively expensive. Biotransformation is an alternative method to obtain chalcone derivatives without harmful compounds.…”
Section: Introductionmentioning
confidence: 99%
“…Biotransformation is an alternative method to obtain chalcone derivatives without harmful compounds. Biocatalysis is often described as a part of green chemistry because it is generally conducted under mild and safe Chemical hydrogenation of a double bond usually requires reagents containing transition metals, e.g., ruthenium or iridium complex [10,11], which are relatively expensive. Biotransformation is an alternative method to obtain chalcone derivatives without harmful compounds.…”
Section: Introductionmentioning
confidence: 99%
“…Recently, Wang, Gülcemal, and co-workers have demonstrated application of iridium complexes in sp 3 C–H functionalization utilizing t -amyl alcohol and toluene as a solvent, though at high temperatures 1113 Likewise, Du and co-workers utilized RhCl(CO)(PPh 3 ) 2 and 1,4-dioxane solvent systems, 14 and other researchers utilized different volatile organic solvents and transition metals such as Fe, Co, and Pd. 1518 In the above strategy, phosphines (as a P-donor ligand) were fundamental in stabilizing the active low-oxidation states.…”
Section: Introductionmentioning
confidence: 99%