Aldehydes and Ketones Formation: Copper-Catalyzed Aerobic Oxidative Decarboxylation of Phenylacetic Acids and α-Hydroxyphenylacetic Acids

Abstract

Aromatic aldehydes or ketones from copper catalyzed aerobic oxidative decarboxylation of phenylacetic acids and α-hydroxyphenylacetic acids have been synthesized. This reaction combined decarboxylation, dioxygen activation, and C-H bond oxidation steps in a one-pot protocol with molecular oxygen as the sole terminal oxidant. This reaction represents a novel decarboxylation of an sp(3)-hybridized carbon and the use of a benzylic carboxylic acid as a source of carbonyl compounds.

Periodic Trends in Highly Dispersed Groups IV and V Supported Metal Oxide Catalysts for Alkene Epoxidation with H2O2

“…82 Epoxidation of the electron-poor styrene is a challenging reaction for d 0 metal oxide catalysts, and yields and epoxide selectivities are correspondingly poorer than for cyclohexene. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 For reaction at 65°C, Figure 5 gives initial rates, epoxide selectivites at ~10% yield, and 6-h selectivites and total yields.…”

MOF Decomposition and Introduction of Repairable Defects Using a Photodegradable Strut

“…Upon exposure to light, NPDAC decomposest o provide am ixture of photoproducts that includes 4-methyl-2nitrophenylacetic acid (3)w ith m/z 194.1,2 -nitro-p-xylene (4) with m/z 302.0 as ad imer ion, and 4-methyl-2-nitrobenzaldehyde (5)w ith m/z 164.0, which was determined by LC/MS analysis and verified by NMR spectroscopy.B ulk photolysis of NPDAC in D 2 Oa lso was monitored by 1 HNMR analysis.A fter 35 min of irradiation, the 1 HNMR spectrum shows am ixture of NPDAC and one major photoproduct, 4-methyl-2-nitrophenylacetic acid (3)t hat is produced by the photodecarboxylation characteristic of m-NPAA compounds. [41][42][43][44] Phenylacetic acids also can be converted directly to benzaldehyde derivatives with variousr eagents, [45][46][47] so the presence of 5 is unremarkable. During the irradiation, the clear yellowish solution becameo paque, which indicatest he possible formation of hydrophobic photoproducts.…”

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp3)–H Bond

“…We were very pleased to find that the yield of 3a could be improved to 58% when the reaction was run in the presence of TBP under MWI at 180 o C for 1 h (entry 16). Lower temperatures, shorter/longer reaction period, or using AIBN, BPO, TBHP, or DCP to replace TBP, led to decreased yield (entries [13][14][15][16][17][18][19][20][21][22]. In order to study the effect of metal salts on this reaction under MWI, it was also carried out in the presence of Cu(OTf) 2 , CuBr 2 , CuBr, CuI, FeCl 2 ·4H 2 O, 13 or FeCl 3 ·6H 2 O.…”

“…1 H and 13 C NMR spectra were determined as CDCl 3 solutions. Chemical shifts were expressed in parts per million (δ) downfield from the internal standard tetramethylsilane and were reported as s cyclopentyl(phenyl)methanone (3m) 16 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 2-ethyl-1-(4-methoxyphenyl)pentan-1-one (3cc), 2-ethyl-1-(4-methoxyphenyl)pentan-1-one (3dd) 33 , and 1-(4-methoxyphenyl)heptan-1-one (3ee) 34 were obtained from the r...…”