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

Abstract

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Additive- and base-free tandem aerobic oxidative cleavage of olefins to esters using bifunctional mesoporous copper-incorporated Al-SBA-15

“…However, the challenge lies in the subsequent conversion of the obtained acids to their corresponding esters. 26 The photocatalytic oxidative cleavage of olefins to esters using tubular carbon nitride was reported by Wang et al Photocatalytic methods are a promising approach for synthesizing esters from olefins, especially when it involves the oxidative cleavage of olefins followed by esterification. In Wang et al 's work, the photocatalytic aerobic oxidative cleavage of olefins to esters using tubular carbon nitride serves as the first step to generate aldehydes and carboxylic acids.…”

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.…”

The Ozone and Hydroperoxide Teamwork: Synthesis of Unsymmetrical Geminal Bisperoxides from Alkenes

“…In addition, ozone is generated from pure oxygen and enters the reaction mixture with an oxygen stream. This can also lead to undesirable olefin oxidation into carbonyl compounds or acids under oxygen in the presence of radical initiators (Scheme c). , …”

“…This can also lead to undesirable olefin oxidation into carbonyl compounds or acids under oxygen in the presence of radical initiators (Scheme 1c). 39,40 The main challenge was to enrich the molecule with peroxide groups, avoiding further overoxidation and peroxide rearrangements. Is it possible to tame the oxidation potential of two strong oxidants (ozone and hydroperoxide) in aggressive media (oxygen stream) and make them work together to create a more energy-rich compound?…”