N-Heterocyclic carbene-catalyzed aerobic oxidation of aryl alkyl alcohols to carboxylic acids

Chemical Constituents with GNMT-Promoter-Enhancing and NRF2-Reduction Activities from Taiwan Agarwood Excoecaria formosana

“…The structure-activity-relationship (SAR) study depicted that more than two galloyl groups connected with the glucose core were necessary for GNMT-promoter-enhancing activity. As isopropyl O-β-(6 -O-galloyl)glucopyranoside (37) and 3-methoxy-4-hydroxyphenyl 1-O-β-d-(6 -O-galloyl)glucopyranoside (39) only had one galloyl group connected with the glucose core, they did not show GNMT-promoter-enhancing activity. Gallic acid 4-O-β-d-(6 -O-galloyl)-glucose (44) is an unusual galloyl glucose compound with one ester linkage group and one ether linkage galloyl group connected with the glucose core.…”

“…[38], 4-methoxybenzoic acid(8) [39], 3-hydroxy-1-(3,5-dimethoxy-4-hydroxyphenyl)propan-1-one(9) [40], 3-hydroxy-1-(4-hydroxy-3-ethoxyphenyl) propan-1-one (10)[41], 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (11)[41], and (2S,3R)-4E-dehydrochebulic acid trimethyl ester (12)[42], a mixture of cerebrosides: gynuramides I-IV(13)(14)(15)(16) [43], three coumarins: scopoletin (17)[44], fraxetin (18)[45], and 6-hydroxy-5,7dimethoxycoumarin (19)[46], six coumarinolignans: cleomiscosins A-D (20-23)[47][48][49], malloapelin A (24)[32,33], and malloapelin B (25)[32,33], three diterpenes: ent-11-α-hydroxy-3-oxo-13-epi-manoyl oxide(26)[50], excoecafolin D (27) [15], and agallochin I (28) [51], two flavonoids: (+)-catechin (29) [52] and kaempferol-3-O-β-d-glucoside (30) [53], six steroids: 6 -(stigmast-5-en-7-one-3-O-β-glucopyransidyl) hexadecanoate (31) [54], (6 -O-palmitoyl) sitosterol-3-O-β-d-glucoside (32) [26], a mixture of βsitosterol (33) and stigmasterol (34) [55], a mixture of 3-O-β-d-glucopyranosyl β-sitosterol (35) and 3-O-β-d-glucopyranosyl stigmasterol (36) [56], and eight galloyl glucoses: isopropyl O-β-(6 -O-galloyl) glucopyranoside (37) [57], 4-hydroxy-3-methoxyphenol 1-O-β-d-(2 ,6 -di-O-galloyl)glucoside (38) [58], 3-methoxy-4-hydroxyphenyl 1-O-β-d-(6 -O-galloyl)glucopyranoside (39) [59], 1,2,3,4,6-penta-O-galloylβ-d-glucose (40) [60], corilagin (41) [61], 1,4,6-tri-O-galloyl-β-d-glucose (42) [62], 1,3,6-tri-O-galloyl-β-dglucose (43) [63], and gallic acid 4-O-β-d-(6 -O-galloyl)-glucose (44) [64]. The phytochemical data of known compounds are available in Supplementary Materials.…”

Metal‐Free Visible‐Light Induced Oxidative Cleavage of C(sp3)−C, and C(sp3)−N Bonds of Nitriles, Alcohols, and Amines

“…[20][21][22][23] Although, various reports are there in the literature for oxidative cleavage of CÀ C(OH) bonds, oxidative dehomologation of alcohols to carbonyls or acids is relatively underdeveloped and these protocols suffered from lower yields and poor selectivity or required high temperature. [24][25][26][27][28][29] In 2015, Yang group reported a metal-free protocol for selective oxidative dehomologation of CÀ C(OH) bond of alcohol with 3-6 equiv. of NaO t Bu at room temperature.…”

“…Development of effective methodologies to cleave and functionalize C−C(OH) bonds is highly important to produce value‐added chemicals from biomass [20–23] . Although, various reports are there in the literature for oxidative cleavage of C−C(OH) bonds, oxidative dehomologation of alcohols to carbonyls or acids is relatively underdeveloped and these protocols suffered from lower yields and poor selectivity or required high temperature [24–29] . In 2015, Yang group reported a metal‐free protocol for selective oxidative dehomologation of C−C(OH) bond of alcohol with 3–6 equiv.…”

Magnetic crosslinked copoly(ionic liquid) nanohydrogel supported palladium nanoparticles as efficient catalysts for the selective aerobic oxidation of alcohols

“…The oxidation of alcohols to carbonyl compounds is an essential transformation in synthetic organic chemistry because of obtained aldehydes and ketones are basic precursors for synthesis of many drugs, vitamins and fragrances [1][2][3]. In particular, the selective oxidation of primary alcohols to the corresponding aldehydes or acids has been widely approved as one of the most important transformations from current chemical industry [4][5][6][7][8][9][10][11][12][13]. In the past two decades, extensive attention has been paid to the use of transition metals as catalysts as a better alternative than the conventional waste-producing oxidation procedures which require stoichiometric amounts of toxic inorganic salts .…”