Highly efficient oxidative cleavage of olefins with O₂ under catalyst-, initiator- and additive-free conditions

Abstract

Described are the first example of 1,4-dioxane-promoted oxidative cleavage of olefins to carbonyls with atmospheric oxygen as the sole oxidant and the maximum conversion was obtained up to 95%. This...

Photoinduced Protocol for Aerobic Oxidation of Aldehydes to Carboxylic Acids under Mild Conditions

“…Molecular oxygen (O 2 ) as a sustainable, non-toxic, and cheap oxidant has demonstrated plenty of merits compared with other oxidants toward environmentally benign chemistry . In particular, the photoinduced aerobic oxidations recently have received considerable attention since they represent a simple and sustainable strategy for organic synthesis. − For example, Wang et al reported a visible-light-induced aerobic oxidation reaction of alkenes for the synthesis of aldehydes and ketones . Recently, He et al disclosed a practical and eco-friendly photocatalytic approach for the switchable synthesis of sulfoxides and sulfones under transition-metal, additive-free, and minimal solvent conditions .…”

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 Under Clean Conditions

“…As far as we know, there are no reports on the synthesis of carboxylic acids from alkenes using O 2 as the sole oxidizing agent without an external initiator, catalyst, and additive. In continuation of our on-going research on selective oxidation with O 2 and green synthesis methods, − we herein reveal a green and efficient one-pot synthesis of aromatic carboxylic acids via 1,2-dibutoxyethane-promoted oxidative cleavage of olefins with molecular oxygen (Scheme d).…”

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

“…However, there is no literature on preparation methods of aromatic acid from aromatic alcohols using O 2 as the sole oxidant under external catalyst-, additive-, and base-free conditions. As the continuation of our interest in selective oxidation utilizing O 2 as the oxidant and environmentally friendly synthesis protocol [ 29 , 42 , 43 , 44 , 45 , 46 , 47 , 48 ], we report an efficient and practical photocatalytic system for the oxygenation of aromatic alcohols to the target acids or ketones without external additives ( Scheme 1 d). Compared with previously reported systems, the protocol was performed successfully with excellent yields at mild reaction conditions, which exhibit a simple post-treatment and could also be applied on one-pot sequential transformation.…”