Metal complexes of aromatic amine n-oxides

Karayannis, Nicholas M.; Pytlewski, L.L.; Mikulski, Chester M.

doi:10.1016/s0010-8545(00)82007-x

Cited by 248 publications

(18 citation statements)

References 401 publications

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“…13,14 The metal-nitrogen and metal-bromide stretching modes in the low frequency IR region are assigned. 1, 15,16 Table 2 presents the extracted infrared spectral data of the adducts.…”

Section: Resultsmentioning

confidence: 99%

Thermochemistry of Morpholine Adducts of Some Bivalent Transition Metal Bromides

Dunstan

2009

J. Chem. Eng. Data

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The adducts [MBr 2 (morph) n ] (where M is Mn(II), Fe(II), Co(II), Ni(II), Cu(II), or Zn(II), morph is morpholine, and n ) 1.5, 2, or 3) were synthesized and characterized by melting points, elemental analysis, thermal analysis, and electronic and IR spectroscopy. From calorimetric studies in solution, the standard enthalpies of formation of the adducts and several thermochemical parameters were determined. The mean standard enthalpies of the metal-nitrogen bond were calculated.

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“…13,14 The metal-nitrogen and metal-bromide stretching modes in the low frequency IR region are assigned. 1, 15,16 Table 2 presents the extracted infrared spectral data of the adducts.…”

Section: Resultsmentioning

confidence: 99%

Thermochemistry of Morpholine Adducts of Some Bivalent Transition Metal Bromides

Dunstan

2009

J. Chem. Eng. Data

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“…The utility of achiral amine N ‐oxides as ligands and their coordination chemistry with metals have been investigated half a century ago. [ 5 ] Nevertheless, the application of chiral amine N ‐oxides in asymmetric catalytic reactions has not been developed until recent decades.…”

Section: Initial Discoverymentioning

confidence: 99%

“…He has received many awards and honors including Higher Education Outstanding Scientific Research Output Awards (Science and Technology) from the Ministry of Education (First class, 2009, 2019), the State Natural Science Award (Second class, 2012), Physical Science Prize of Future Science Prize (2018), Huang Yaozeng Metal Organic Chemistry Award (2018), Ho Leung Ho Lee Foundation Prize for Scientific and Technological Progress (2019), the National Innovation and Competition Prize of China (2020), Tan Kah Kee Science Awards (2020), etc . Chemistry developed in his laboratory Research in Feng's group is centered on the field of organic synthesis and catalysis, including the design of chiral catalysts and ligands, development of asymmetric reactions, and synthetic applications of optically active compounds. [ 1‐8 ] Inspired by the catalytic modes of enzymes, several novel classes of chiral catalysts have been developed from commercially available amino acids, including chiral N , N '‐dioxide organocatalysts and ligands ( A ), chiral guanidine‐amide organocatalysts and ligands ( B ), bispidine‐based chiral diamines ( C ), organic salts ( D ) and others. Especially, Feng N , N '‐dioxide was demonstrated as privileged ligands for more than 50 types of asymmetric reactions, covering diverse areas of catalysis.…”

Section: Acknowledgementmentioning

confidence: 99%

“…Research in Feng's group is centered on the field of organic synthesis and catalysis, including the design of chiral catalysts and ligands, development of asymmetric reactions, and synthetic applications of optically active compounds. [ 1‐8 ] Inspired by the catalytic modes of enzymes, several novel classes of chiral catalysts have been developed from commercially available amino acids, including chiral N , N '‐dioxide organocatalysts and ligands ( A ), chiral guanidine‐amide organocatalysts and ligands ( B ), bispidine‐based chiral diamines ( C ), organic salts ( D ) and others. Especially, Feng N , N '‐dioxide was demonstrated as privileged ligands for more than 50 types of asymmetric reactions, covering diverse areas of catalysis.…”

Section: Acknowledgementmentioning

confidence: 99%

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Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Wang

2021

Chin. J. Chem.

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Feng ligand | N,N'-Dioxide | O ligands | Asymmetric catalysis | Lewis acids Catalysts and ligands possessing the great ability to tolerate over a wide range of mechanistically unrelated reactions are remarked as "privileged", which are rather scarce but extremely meaningful in asymmetric catalysis. Feng and co-workers have developed a library of conformationally flexible, C 2-symmetric N,N'-dioxide amide compounds with original design and featured structure (named as Feng ligand now). They were initially reported as chiral organocatalysts in 2005 and have been further developed as a new class of privileged chiral ligands since 2006. Tremendous success, including versatile coordination chemistry with plenty of metal sources (main-group metals, transition metals, and rare-earth metals), a truly broad scope of asymmetric reactions (more than 50 types), diverse areas of catalysis (organocatalysis, Lewis-acid catalysis, bimetallic relay catalysis, and photocatalysis), numerous synthetic applications of bioactive compounds, has been achieved using Feng N,N'-dioxide. Besides, they demonstrate that chiral ligands with conformationally flexible property can offer excellent chiral environment as well, which challenges the conventional idea preferring rigid structures in the design of chiral ligands. Herein, we briefly introduced the discovery of Feng ligand and the millstones during the development. We also covered the successful applications of Feng ligand by other scientists as well as novel chiral ligands inspired by them. Contents 1. Introduction 969 2. Initial Discovery 970 3. Representative Applications 971 3.1. Classical asymmetric reactions 971 3.2. Novel asymmetric reactions 975 4. Studies by Other Groups 977 4.1. Reactions using Feng ligand 977 4.2. Novel chiral ligands inspired by Feng ligand 980 5. Conclusions 980

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“…[1] Pyridine N-oxides are highly versatile compounds, since they possess notable nucleophilicity and basicity, propensities which allow them to function as Lewis base catalysts and as ligands for metal complexes. [2,3] In each case, an oxygen atom serves as a basic/ligating site. Accordingly, various chiral pyridine N-oxides have been developed and shown to be effective as Lewis base catalysts and ligands for many useful asymmetric transformations.…”

Section: Introductionmentioning

confidence: 99%

Helical Chiral Pyridine N‐Oxides: A New Family of Asymmetric Catalysts

Chen

Takenaka

2009

Chemistry A European J

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Optically active chiral alkyl chlorides are valuable compounds because of their bioactivity and versatile synthetic utility. Accordingly, the ring opening of epoxides with a chloride nucleophile stands as an important goal in asymmetric catalysis. We describe herein recent advances in the design and development of chiral pyridine N-oxide catalysts for the enantioselective synthesis of chlorohydrins.

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Metal complexes of aromatic amine n-oxides

Cited by 248 publications

References 401 publications

Thermochemistry of Morpholine Adducts of Some Bivalent Transition Metal Bromides

Thermochemistry of Morpholine Adducts of Some Bivalent Transition Metal Bromides

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Helical Chiral Pyridine N‐Oxides: A New Family of Asymmetric Catalysts

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