Biomimetic Aerobic Epoxidation of Alkenes Catalyzed by Cobalt Porphyrin under Ambient Conditions in the Presence of Sunflower Seeds Oil as a Co-Substrate

Abstract

In this work, a mild and sustainable catalytic aerobic epoxidation of alkenes catalyzed by cobalt porphyrin was performed in the presence of sunflower seeds oil. Under ambient conditions, the conversion rate of trans-stilbene reached 99%, and selectivity toward epoxide formation was 88%. The kinetic studies showed that the aerobic epoxidation followed the Michaelis−Menten kinetics. Mass spectroscopy and in situ electron spin resonance indicated that linoleic acid was converted to fatty aldehydes via hydroperoxide intermediates. A plausible mechanism of epoxidation of alkenes was accordingly proposed.

A Pyridinium‐Pyridinium Zinc(II) Porphyrin Ion Porous Organic Polymer as Efficient Heterogeneous Catalyst for Cycloaddition of Epoxides with CO2

“…[5] In particular, CO 2 cycloaddition with epoxides has been one of the most concerned reaction due to its 100 % atom efficiency. [6][7][8][9][10] Metalloporphyrins show excellent catalytic performance in many fields, such as catalytic oxidation/reduction, [11,12] and photocatalysis. [13,14] In particular, the CO 2 cycloaddition reaction catalyzed by metalloporphyrins has attracted growing attention.…”

“…Metalloporphyrins show excellent catalytic performance in many fields, such as catalytic oxidation/reduction, [11,12] and photocatalysis [13,14] . In particular, the CO 2 cycloaddition reaction catalyzed by metalloporphyrins has attracted growing attention [15] .…”

Highly efficient and robust aerobic co-oxidation of olefins and aldehydes over CoOx dispersed within hierarchical silicalite-1 zeolites

“…[10][11][12][13][14] In the past several decades, both homogeneous and heterogeneous co-oxidation catalysts based on various transition metal elements, such as Mn, Fe, Co, Ni, Cu and Ru, have been widely reported in the literature. [15][16][17][18][19][20][21][22] Yet, homogeneous catalysts are difficult to be separated and reused, while the rational design and construction of heterogeneous catalysts with high distribution and thermal stability of transition metal species at the same time is still a big challenge, which needs profound understanding at the atomic scale. Notably, among various solid catalysts, metal nanoparticle loaded catalysts with a narrow size distribution show superior catalytic application potential in co-oxidation reactions.…”

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

“…Besides their low cost and low toxicity, the choice of these metals is related to their known ability to activate dioxygen in natural processes catalyzed by metal-containing enzymes [ 29 – 30 ]. Despite that various homogeneous [ 31 – 32 ] and heterogeneous [ 33 – 37 ] Co-based catalysts have been applied to the epoxidation of alkenes, however, most of the reported methods lead to unsatisfactory yield, low selectivity, or limited substrate scope. Suib et al [ 38 ] reported on the synthesis of mesoporous Co 3 O 4 for the catalytic epoxidation of a variety of alkenes as an interesting heterogeneous system.…”