KI‐I₂‐DMSO: An Improved Microwave‐Assisted Selective Oxidation of Alkenes into 1,2‐Diketones

Abstract

The microwave assisted catalytic oxidation of olefins into diketones is a remarkable effort. A new metal free, efficient catalytic system was developed for the oxidation of alkenes into α‐diketones using KI‐I2‐DMSO under microwave irradiation. With various challenging functional groups such as stilbenes, simple alkenes, alkynes, phenanthrene and 1,4‐distyrylbenzene, this environment friendly approach afforded to its corresponding products in moderate to excellent yields in 5–12 minutes under the optimized condition. The resulting α‐diketone from chlorobenzil was found to undergo Suzuki‐Miyaura cross‐coupling reaction to obtain desired product in high yields. Thus, this methodology promises to be a cheaper and rapid synthesis for the production of different building blocks in the near future.

Total synthesis of huperserratines A and B

“…Our attempts to directly oxidize the double bond to the diketone were unsuccessful. 37,38 Fortunately, diol 12 was obtained by dihydroxylation of macrocyclic 4 in the presence of osmium tetroxide and NMO in 85% yield (dr = ∼4 : 1). 39 The N-methyl group was installed through a one-pot detosylation/reductive amination process 40 in readiness for the Swern oxidation 41 to deliver triketones 13 and 14 in 28% and 24% yields from two steps, respectively.…”

Exploiting silver trifluoromethanesulfonate as efficient and reusable catalyst for the synthesis of dihydropyrimidine derivatives under different reaction environments

“…Since we have carried out many conventionally heating and microwave-assisted reactions under different environments, so the energy consumed by the reactions was calculated as we mentioned in our earlier report. [24] Herein, when the reaction reached its respective yield, we examined the energy consumptions as well as energy efficiency by the aforesaid reaction (Scheme 2). Apparently, it has been observed that for this reaction, the microwave-irradiated method is far more energy efficient and preferable than conventional heating method.…”

Imidazoles and Oxazoles from Lapachones and Phenanthrene‐9,10‐dione: A Journey through their Synthesis, Biological Studies, and Optical Applications

“…For example, Bordoloi and Tamuli described the oxidation of phenanthrene ( 23 ) via KI‐I 2 ‐DMSO‐catalyzed under microwave assistance to provide phenanthrenequinone ( 14 ) in 95 % yield in only 9 minutes (Scheme 3). [18c] Another approach to synthesizing phenanthrenequinone ( 14 ) involves the intramolecular cyclization of bisaryl derivatives bearing different substituents (Scheme 3). [19] For example, Ray and co‐worked reported the cross dehydrogenative coupling of 24 , under CuCl catalysis to achieve phenanthrenequinone ( 14 ) in 85 % yield at room temperature after 1 h of reaction [19a] .…”