The hydroxylation and amidation of equilenin acetate catalyzed by chloro[5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(iii)

Yang, Jerry; Weinberg, Richard; Breslow, Ronald

doi:10.1039/b000463o

Cited by 99 publications

(66 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In all, the procedures outlined by Che and Katsuki make available a number of allylic and benzylic sulfonamides from inexpensive, unfunctionalized starting materials. Breslow and Che have both demonstrated the utility of ruthenium-and manganese catalysts for the intermolecular amination of steroids, though improvements to the efficiency of such reactions are still required [54,58,59]. …”

Section: Intermolecular C-h Amination With Other Metalsmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

View full text Add to dashboard Cite

17 Rhodium(II)-Catalyzed Oxidative Amination 380 Scheme 17.1 Copper-catalyzed decomposition of arylsulfonyl azides. Scheme 17.2 Intramolecular C-H amination of an iminoiodinane. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 381 Scheme 17.3 Metal porphyrin-catalyzed allylic amination. Scheme 17.4 C-H amination by a radical-rebound mechanism. 17 Rhodium(II)-Catalyzed Oxidative Amination 382 Scheme 17.5 Rhodium-catalyzed N-atom transfer using NsN=IPh. Scheme 17.6 Stereospecific C-H amination under rhodium-catalyzed conditions. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 383 Scheme 17.7 Radical clock study of metallo-nitrene C-H insertion. Scheme 17.8 Intermolecular C-H insertion by chiral rhodium catalysts. 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 385 Scheme 17.11 Allylic and benzylic amination using PhI(OAc) 2 . 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 387 Tab. 17.1 C-H amination of 18 carbamate esters. Entry Substrate Product Entry Substrate Product 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 389 Scheme 17.14 Ketone formation by 28 alcohol-derived carbamates. 17.7 Enantioselective C-H Insertion with Sulfamate Esters 401 Scheme 17.29 Oxidative cyclization of unsaturated sulfonamides. Scheme 17.30 Preliminary investigations of asymmetric C-H amination. 17.11 Applications of C-H Amination in Synthesis 407 17.11 Applications of C-H Amination in Synthesis 409 Scheme 17.39 Asymmetric synthesis of (-)-tetrodotoxin. 17 Rhodium(II)-Catalyzed Oxidative Amination 410 Scheme 17.40 Nucleophilic ring opening of N-acylated oxathiazinanes. Scheme 17.41 Nickel-catalyzed cross-coupling of phenol-derived sulfamate esters.

show abstract

Section: Intermolecular C-h Amination With Other Metalsmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

View full text Add to dashboard Cite

show abstract

“…[5,6] In contrast, metal-catalyzed arene amination is practically unknown, [6] even though free organonitrenes will readily add to aromatics. [7] Substoichiometric and unselective naphthalene amination by an uncharacterized adduct of iron(ii) chloride and chloramine-T has been reported, [8] along with a handful of possibly analogous organometallic ligand transformations.…”

mentioning

confidence: 99%

Intramolecular Aromatic Amination through Iron‐Mediated Nitrene Transfer

2003

View full text Add to dashboard Cite

“…Dodd and Dauban 11 demonstrated the copper-catalyzed aziridination of 1-pregnene-3, 20-dione in 53% yield with PhI=NSes (Ses = 2-(trimethylsilyl) ethanesulfonyl). Breslow 12 reported the amidation of equilenin acetate with PhI=NTs catalyzed by [Mn (TPFPP) Cl] (TPFPP = meso-tetrakis (pentafluorophenyl)porphyrinato dianion) in 47% yield. Che recently reported the amidation of chlosteryl acetate catalyzed by a chiral Ru(II)-salen complex 13 and a chiral Mn porphyrin 2i with high diasteroselectivities.…”

Section: Resultsmentioning

confidence: 99%

“…Amidation of ∆ 5 -steriod derivatives with "PhI(OAc) 2 + TsNH 2 " catalyzed by polymer-supported metalloporphyrins 3a and 3b. 12 (Strem) were used as received. All alkenes of the highest quality available from commercial were purified as literature.…”

Section: Resultsmentioning

confidence: 99%

Aziridination and amidation reaction mediated by polymer-supported metalloporphyrins with PhI(OAc)2 and TsNH2

Zhou¹,

Zhao²,

Yang³

et al. 2005

Arkivoc

View full text Add to dashboard Cite

Manganese and ruthenium 5, 10, 15-tris(tolyl)-20-(4-hydroxyphenyl)porphyrins covalently attached to Merrifield's peptide resin(MPR) were prepared respectively. The catalysts efficiently catalyzed the aziridination/amidation of simple hydrocarbons and ∆ 5 -steroid derivatives with PhI(OAc) 2 and TsNH 2 . Moderate to excellent yields were obtained under mild reaction conditions. The catalysts 3a and 3b exhibit different diasteroselectivities towards the ∆ 5 -steroid derivatives, the former shows α-selectivity   and the later shows β-selectivity under certain reaction conditions.

show abstract

The hydroxylation and amidation of equilenin acetate catalyzed by chloro[5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(iii)

Cited by 99 publications

References 11 publications

Rhodium(II)‐Catalyzed Oxidative Amination

Rhodium(II)‐Catalyzed Oxidative Amination

Intramolecular Aromatic Amination through Iron‐Mediated Nitrene Transfer

Aziridination and amidation reaction mediated by polymer-supported metalloporphyrins with PhI(OAc)2 and TsNH2

Contact Info

Product

Resources

About