The
oxidative cleavage of alkenes to the corresponding aldehydes using
new amphiphilic carbon quantum dots (A-CQDs) as a pseudohomogeneous
carbocatalyst is achieved for the first time through green and sustainable
chemical processes. In this work, we successfully design a recyclable
pseudohomogeneous catalyst based on A-CQDs, which is decorated with
1-aminopropyl-3-methyl-imidazolium chloride and stearic acid. The
functionalization is conducted to introduce a hydrophilic/hydrophobic
functionality on the surface of the catalyst to achieve high catalyst
availability in polar and nonpolar media with the green goal of eliminating
organic (co)solvents and additives. This amphiphilic carbocatalyst
provides high mass transferability to the biphasic system, which is
beneficial to promoting the oxidative cracking of a variety of olefins
into corresponding aldehydes with a substrate/A-CQD ratio of 150.
Around 87% of the substrates are converted to the related aldehydes
using the carbocatalyst in the presence of H2O2, in pure water, without using a phase-transfer catalyst or any additives
and organic solvents, which is comparable with the current metal-based
cleavage systems. Surprisingly, A-CQDs exhibit high catalytic activity
for the scission of electron-deficient CC bond of coumarin
derivatives, accompanied by the cleavage of C–O bonds to produce
the corresponding salicylaldehyde derivatives without overoxidation
to acid. As a brief conclusion, A-CQDs exhibit high conversion efficiency
without significant loss of activity even after six catalytic cycles.
The conversion of alkenes into aldehydes is fast and high-throughput
without overoxidation to acids and is accompanied by excellent solubility
and stability in various solvents. Moreover, the product and the catalyst
are recoverable from the reaction medium by simple extraction. So,
this pseudohomogeneous carbocatalyst promises new horizons in imminent
“catalytic
age”. All in all, this paper provides a significant and novel
advancement in carbocatalyst chemistry.