A Unique Peroxide Formation Based on the Mn(III)‐Catalyzed Aerobic Oxidation.

Kumabe, Ryoukou; Nishino, Hiroshi

doi:10.1002/chin.200418135

Cited by 1 publication

(2 citation statements)

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“…Quinone [25] and quinolinone [26] derivatives were found to be useful reagents to give free radical cyclizations with active methylene compounds. A great variety of free radical cyclizations of 1,4-napthaquinones with -dicarbonyl compounds that afford polycyclic compounds was investigated by Chuang and co-workers [25].…”

Section: O Armentioning

confidence: 99%

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Manganese(III) Acetate: A Versatile Reagent in Organic Chemistry

Demir¹,

Emrullahoğlu

2007

COS

106

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Free radical reactions have become increasingly important, as well as a very attractive tool, in organic synthesis within the last two decades, due to their powerful, selective, specific, and mild reaction abilities. Mn(OAc)3 mediated oxidative free radical reactions have been extensively developed in the last twenty years. Numerous regio-, chemo-, and stereoselective synthetic methods have been developed in both inter-and intramolecular reactions, and have detailed the progress of Mn(OAc)3 mediated oxidative free radical reactions since the end of the 19 th century. The new literature about the new synthetic methods on Mn(OAc)3 mediated carbon-carbon bond formation and carbon-oxygen bond formation reactions has not been extensively reviewed. The present paper summarizes the recent developments in oxidative free radical reactions mediated by Mn(OAc)3. Mn(OAc)3 mediated reactions of conjugated systems (e.g., alkenes, alkynes, 1,3-alkadienes, l,3-alkadiynes, 1-alken-3-ynes) with -dicarbonyl compounds, Mn(OAc)3 mediated alkylation, such as the oxidative addition of an aldehyde or ketone to alkenes, Mn(OAc)3 mediated free-radical cyclization of alkenes with active methylene compounds in the presence of oxygen to afford the cyclic peroxides; lactone synthesis by the Mn(OAc)3 mediated oxidative addition of carboxylic acids to alkenes, Mn(OAc)3 mediated cyclization of -(methylthio)acetamides, enamides, and -keto carboxamides to afford cyclic products.Mn(OAc)3 oxidative free-radical cyclizations of allylic -dicarbonyl compounds, for example, the cyclization of allylic -ketoesters to afford the corresponding -lactone. The reaction of alkenes with sodium azide in the presence of acetic acid was investigated to afford 1.2-diazides. The selective oxidation of enones led to '-acetoxy-enones by Mn(OAc)3 oxidation. In general, Mn(OAc)3 oxidations are characterized by higher '-regioselectivity and chemical yields, and milder reaction conditions, in turn tolerating many sensitive functional groups. The use of Mn(OAc)3 in combination with other carboxylic acids or manganese(II) carboxylates extends this methodology to the preparation of a variety of '-acyloxyenones that are otherwise inaccessible in a one-step procedure.

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Section: O Armentioning

confidence: 99%

“…As shown in Scheme 14, the oxidative cyclization of 4hydroxy-2-quinolinone derivatives with 1,1-disubstituted ethene furnished the tricyclic 3-(2,2-diarylethenyl)quinolinone-2,4-diones in good yield [26].…”

Section: O Armentioning

confidence: 99%