Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-Diketones

Abstract

The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon experimental observations, a plausible mechanism is proposed.

Aminocatalytic Cross‐Coupling Approach via Iminium Ions to Different CC Bonds

“…[11] Much literature is available on the generation of symmetric benzils, but synthesis of unsymmetrical 1,2-diones has also attracted significant attention in the past few years. Synthetic strategies for their preparation include the oxidation of alkynes, [12] alkenes, [13] and amethylene ketones, [14] decarboxylation of 1,3-diketones, [15] and some others. [16] Compared to previous reports, our method is the mildest promising approach to a-diones with wide substrate scope.…”

6.13 Use of Carbonyl Derivatives for Heterocyclic Synthesis

“…[33][34][35] Another strategy, which allows installation of specific 4-and 5-position imidazole groups, produces the diketone from the corresponding 1,2-diol and subsequent oxidation. This approach allows one to utilize well-established Grubbs cross-metathesis protocols to synthesize the alkene.…”

CuI‐Catalyzed Synthesis of Propargyl Hydroperoxides Using Molec­ular Oxygen and Hydroxylamines

“…Oxidation methods that exploit molecular oxygen are advantageous because oxygen is the most abundant and sustainable source of oxygen atoms 1,2. The 1,2‐dioxygenation of alkenes using molecular oxygen is uncommon,3–5 however, often requiring the use of dialkyl peroxides as initiators 6–13. To solve this issue, the 1,2‐dioxygenations of alkenes using N ‐hydroxyphthalimide (NHPI) and N ‐hydroxybenzotriazole (HOBt) have been developed 14–17.…”