1,2-Diethoxyethane catalyzed oxidative cleavage of gem-disubstituted aromatic alkenes to ketones under minimal solvent conditions

Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols

“…This result suggests that the presence of O 2 is important for the intermolecular oxidative coupling reaction. 22 Furthermore, a radical trapping experiment by using 2,2,6,6-tetramethylpiperidinooxy (TEMPO, 1.0 equiv.) as a radical inhibitor provided clear evidence that the reaction might not proceed in a radical manner ( Scheme 2C ).…”

Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

“…The yield of 2a remained at 99% when the reaction temperature dropped to 110 C, but lower yield of 78% was observed at 100 C (entries [17][18]. Shorter reaction time was also attempted, the results revealed that the yield remained at 99% at 8 hours (entries [19][20]. When the reaction was performed under air atmosphere, the yield decreased to 35% (entry 21).…”

“…Based on the control experiments and reported work, 20 a plausible reaction pathway was proposed as shown in Scheme 5 . Firstly, PEGDME was oxidized by O 2 to produce a peroxyl radical 3a′.…”

“…Very recently, although a 1,2-diethoxyethane catalysed oxidative scission of olefins to ketones by air has been achieved, the olefins are limited to gem -disubstituted aromatic alkenes. 20 Therefore, developing a wide applicable strategy for the oxidative scission of olefins to aldehydes and ketones is highly desirable but still remains a challenge.…”

Bis(2-methoxyethyl)ether promoted intramolecular acceptorless dehydrogenative coupling to construct structurally diverse quinazolinones by molecular oxygen

“…5 In 2019, the dioxane-mediated aerobic oxidation of isoindolines into isoindolinones has also been realized (Scheme 1b). 6 Recently, the oxidative cleavage of gem -disubstituted aromatic alkenes into ketones by molecular oxygen mediated by 1,2-diethoxyethane 7 or poly(ethylene glycol)dimethyl ether 8 was independently reported by He's group and our group (Scheme 1c). So far, the application of the ether/O 2 system is limited to oxidative dehydrogenation, oxidative cleavage, and oxygen insertion.…”