Manganese complexes with non-porphyrin N<sub>4</sub>ligands as recyclable catalyst for the asymmetric epoxidation of olefins

Maity, Nabin Ch.; Bera, Prasanta Kumar; Ghosh, Debashis; Abdi, Sayed H. R.; Kureshy, Rukhsana I.; Khan, Noor‐ul H.; Bajaj, Hari C.; Suresh, Eringathodi

doi:10.1039/c3cy00528c

Cited by 35 publications

(25 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The mcp ligand was prepared on the basis of the literature method without further modification . One equivalent of Ni(ClO 4 ) 2 ⋅ 6 H 2 O (0.472 g, 1.278 mmol) was added to a CH 3 CN (35 mL) solution containing mcp ligand (0.414 g, 1.278 mmol).…”

Section: Methodsmentioning

confidence: 99%

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

et al. 2016

View full text Add to dashboard Cite

A new mononuclear nickel complex, featuring two cis‐relative labile sites, is reported as a homogeneous electrocatalyst for water oxidation in a neutral phosphate buffer. The water oxidation catalysis can be initiated at a moderate overpotential of approximately 0.48 V. Mechanistic studies reveal that the oxidation of water by a two‐electron oxidized species of the nickel catalyst is feasible, with formation of a peroxide intermediate through intramolecular O−O coupling. Interestingly, it has been found that the buffer base (HPO42−) plays a dual role in the catalytic system: it acts as a proton acceptor to expedite proton‐coupled electron transfer (PCET) during catalysis, but it also suppresses the electrocatalysis through an anation process.

show abstract

Section: Methodsmentioning

confidence: 99%

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

et al. 2016

View full text Add to dashboard Cite

show abstract

“…aEpoxidation procedures: entry 1 (ref (20a)), entry 2 (ref (21)), entry 3 (ref (22)), entry 4 (ref (23)), entry 5 (ref (24)), entry 6 (ref (25)), entry 7 (ref (26)), and entry 8 (ref (27)).bCombined, isolated yield.cMeasured by NMR.d>90% unreacted 1 recovered.ena, not applicable or no analysis.…”

Section: Resultsmentioning

confidence: 99%

Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides

Kumar

Jat

et al. 2014

J. Org. Chem.

View full text Add to dashboard Cite

Methyltrioxorhenium (MTO) complexed with pyridine was shown to be a highly effective catalyst for the regioselective monoepoxidation of conjugated di- and trienes using 30% H2O2 at or below room temperature. The resultant allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The site of epoxidation was dependent upon olefin substitution, olefin geometry (Z vs E), and the presence of electron-withdrawing substituents on adjacent carbons. For 1-acyl(silyl)oxypenta-2,4-dienes, epoxidation of the distal olefin was generally favored in contrast to the adjacent regioselectivity characteristic of Sharpless, peracid, and other directed epoxidations of hydroxylated dienes.

show abstract

“…vs. substrate) in the presence of acetic acid additive (5 equiv.). More recently, Abdi with co‐workers reported structurally related complex 4d (Figure ), which was examined in epoxidations of different olefins with hydrogen peroxide and demonstrated high efficiencies (800‐1000 TN) and moderate to good enantioselectivies (43‐88 % ee ) …”

Section: Asymmetric Epoxidation Of Olefins On Mn(ii) Aminopyridine Comentioning

confidence: 99%

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo‐ and Stereoselective Oxidations with H₂O₂

Ottenbacher

Talsi

Bryliakov

2017

The Chemical Record

View full text Add to dashboard Cite

In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of CÀH groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.

show abstract

Manganese complexes with non-porphyrin N₄ligands as recyclable catalyst for the asymmetric epoxidation of olefins

Cited by 35 publications

References 38 publications

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo‐ and Stereoselective Oxidations with H₂O₂

Contact Info

Product

Resources

About

Manganese complexes with non-porphyrin N4ligands as recyclable catalyst for the asymmetric epoxidation of olefins

Cited by 35 publications

References 38 publications

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO42− in Catalysis

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO42− in Catalysis

Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo‐ and Stereoselective Oxidations with H2O2

Contact Info

Product

Resources

About

Manganese complexes with non-porphyrin N₄ligands as recyclable catalyst for the asymmetric epoxidation of olefins

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

A Nickel(II) Complex as a Homogeneous Electrocatalyst for Water Oxidation at Neutral pH: Dual Role of HPO₄²⁻ in Catalysis

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo‐ and Stereoselective Oxidations with H₂O₂