Radical reactions of [60]fullerene with β-enamino carbonyl compounds mediated by manganese(<scp>iii</scp>) acetate

Wang, Guan‐Wu; Yang, Hai‐Tao; Miao, Chun‐Bao; Yu, Xu; Liu, Fei

doi:10.1039/b604626f

Cited by 60 publications

(27 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, since MnA C H T U N G T R E N N U N G (OAc) 3 is poorly soluble in organic solvents, harsh reaction conditions together with a tedious separation procedure are normally required. [88] In order to establish efficient and milder reaction conditions, Wang and co-workers investigated novel manganeseA C H T U N G T R E N N U N G (III) acetate dihydrate [Mn-A C H T U N G T R E N N U N G (OAc) 3 ·2 H 2 O]-mediated intermolecular radical additions of 1,3-cyclohexanediones to in situ generated imines under solvent-free conditions, promoted by the ball milling technique. In this study, a variety of solid aromatic aldehydes 13 were reacted in a vibration ball mill (30 Hz) with solid 4-methylaniline (85) affording quantitatively the corresponding imines after 1 h. These in situ generated imines were then directly reacted with 1,3-cyclohexanediones in the presence of MnA C H T U N G T R E N N U N G (OAc) 3 ·2 H 2 O using a ball mill (Scheme 27).…”

Section: Radical Additions To Imines Mediated By Mn(iii)mentioning

confidence: 97%

Solvent‐Free Carbon‐Carbon Bond Formations in Ball Mills

et al. 2007

View full text Add to dashboard Cite

show abstract

Section: Radical Additions To Imines Mediated By Mn(iii)mentioning

confidence: 97%

Solvent‐Free Carbon‐Carbon Bond Formations in Ball Mills

et al. 2007

View full text Add to dashboard Cite

show abstract

“…Thus, Mn(OAc) 3 behaves as a Lewis acid as well as a radical initiator, and alters the regioselectivity. 27 Recently, they found that in the Mn(OAc) 3mediated reaction with 1-(pyridin-2-yl)-enones, replacement of 1,3-cyclohexanediones with their b-enamino carbonyl compounds afforded dihydrobenzofuran derivatives, instead of the expected 2-acyl-3-aryl-indole derivatives (Scheme 8). 28 The addition of a base such as N,N-dimethylaminopyridine (DMAP) improved the product yields, and N-unsubstituted b-enamino carbonyl compounds performed better than their N-substituted counterparts.…”

Section: Fecl 3 -Promoted Oxidative Homocoupling Of Phenolsmentioning

confidence: 99%

Mechanochemical organic synthesis

2013

Self Cite

View full text Add to dashboard Cite

Recently, mechanical milling using a mixer mill or planetary mill has been fruitfully utilized in organic synthesis under solvent-free conditions. This review article provides a comprehensive overview of various solvent-free mechanochemical organic reactions, including metal-mediated or -catalyzed reactions, condensation reactions, nucleophilic additions, cascade reactions, Diels-Alder reactions, oxidations, reductions, halogenation/aminohalogenation, etc. The ball milling technique has also been applied to the synthesis of calixarenes, rotaxanes and cage compounds, asymmetric synthesis as well as the transformation of biologically active compounds.

show abstract

“…[60]Fullerenolactones (R = H, Me, Ph) were prepared in 18-41% yields by regioselective Mn(OAc) 3 mediated oxidative cyclocondensation of C-60 with carboxylic acids, carboxylic anhydrides, or malonic acids in the presence of 4-(dimethylamino)pyridine. In a recent example, radical reactions of [60]fullerene with -enamino carbonyl compounds mediated by Mn(OAc) 3 were reported [117]. In a recent example, radical reactions of [60]fullerene with -enamino carbonyl compounds mediated by Mn(OAc) 3 were reported [117].…”

Section: Manganese(iii) Acetate Mediated Reactions With Fullerenementioning

confidence: 99%

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

Demir¹,

Emrullahoğlu

2007

COS

101

View full text Add to dashboard Cite

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.

show abstract

Radical reactions of [60]fullerene with β-enamino carbonyl compounds mediated by manganese(iii) acetate

Abstract: Manganese(III) acetate dihydrate-mediated reactions of [60]fullerene with beta-enamino carbonyl compounds afforded [60]fullerene-fused pyrroline derivatives, of which the nitrogen atom is directly connected to the fullerene cage. A possible reaction mechanism is proposed.

Cited by 60 publications

References 31 publications

Solvent‐Free Carbon‐Carbon Bond Formations in Ball Mills

Solvent‐Free Carbon‐Carbon Bond Formations in Ball Mills

Mechanochemical organic synthesis

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

Contact Info

Product

Resources

About