Diazoalkane complexes of tungsten from the condensation of hydrazido Complexes with Ketones

Bevan, Peter C.; Chatt, J.; Hidai, Masanobu; Leigh, G. J.

doi:10.1016/s0022-328x(00)91210-5

Cited by 54 publications

(9 citation statements)

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“…Chatt and coworkers also reported similar reactivity of hydrazido(1-), W–NH–NH 2 , along with hydrazido(2-) complexes . With hydrazido(1-) complexes, the corresponding condensation products, W–NH–NCR 2 were obtained from ketones with a catalytic amount of acid.…”

Section: N–x Bond Formation With Retention Of the N–n Bondmentioning

confidence: 76%

“…Chatt and coworkers also reported similar reactivity of hydrazido(1-), W−NH−NH 2 , along with hydrazido(2-) complexes. 63 With hydrazido(1-) complexes, the corresponding condensation products, W−NH−NCR 2 were obtained from ketones with a catalytic amount of acid. In addition, [WX 2 (NNH 2 )(PMe 2 Ph) 3 ] exhibited the same condensationtype reactivity with ketones, which was subsequently reported by Hidai and coworkers (Scheme 6).…”

Section: Interaction Of N 2 With Transition Metalsmentioning

confidence: 99%

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Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

2020

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The functionalization of coordinated dinitrogen to form nitrogen–element bonds en route to nitrogen-containing molecules is a long-standing challenge in chemical synthesis. The strong triple bond and the nonpolarity of the N2 molecule pose thermodynamic and kinetic challenges for promoting reactivity. While heterogeneous, homogeneous, and biological catalysts are all known for catalytic nitrogen fixation to ammonia, the catalytic synthesis of more complicated nitrogen-containing organic molecules has far less precedent. The example of silyl radical additions to coordinated nitrogen to form silylamines stands as the lone example of a catalytic reaction involving N2 to form a product other than ammonia. This Review surveys the field of molecular transition metal complexes as well as recent boron examples for the formation of nitrogen–element bonds. Emphasis is placed on the coordination and activation modes of N2 in the various metal compounds from across the transition series and how these structures can rationally inform reactivity studies. Over the past few decades, the field has evolved from the addition of carbon electrophiles in a manner similar to that of protonation reactions to more organometallic-inspired reactivity, including insertions, 1,2-additions, and cycloadditions. Various N–C, N–Si, and N–B bond-forming reactions have been discovered, highlighting that the challenge for catalytic chemistry is not in the reactivity of coordinated dinitrogen but rather removal of the functionalized ligand from the coordination sphere of the metal.

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Section: N–x Bond Formation With Retention Of the N–n Bondmentioning

confidence: 76%

Section: Interaction Of N 2 With Transition Metalsmentioning

confidence: 99%

Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

2020

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“…Similar reaction of 2b also gave 2,4,6-trimethylpyridine and ammonia in good yields. These results are in a sharp contrast to the fact that a related (1-pyrrolyl)imido complex [WBr 2 (NNC 4 H 4 )(CO)(PMe 2 Ph) 2 ] undergoes a similar base-promoted reaction to afford 1-aminopyrrole through the selective W−N bond cleavage 3e …”

mentioning

confidence: 66%

Synthesis of Tungsten (1-Pyridinio)imido Complexes: Facile N−N Bond Cleavage To Form Pyridine from Coordinated Dinitrogen¹

et al. 1996

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Tungsten hydrazido complexes [WCl2(NNH2)(L)(PMe2Ph)2] (L = CO, C2H4) derived from dinitrogen complex [W(N2)2(PMe2Ph)4] reacted with 2,4,6-trimethylpyrylium or 2,6-diethoxycarbonyl-4-phenylpyrylium tetrafluoroborate to give novel (1-pyridinio)imido complexes in high yields, which were spectroscopically and crystallographically characterized. The (2,4,6-trimethylpyridinio)imido complexes [WCl2(NNC5H2Me3)(L)(PMe2Ph)2][BF4] underwent facile and selective N−N bond cleavage upon treatment with KOH or cobaltocene at room temperature to yield 2,4,6-trimethylpyridine in high yields.

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“…These have been previously prepared by Behrens,3 though very little further work has been carried out on them. 4 An unusual feature of these complexes is that the infrared spectra of the solid complexes show two v(CO) absorptions at very low frequencies for terminal CO ligands (ca. 1770 and ca.…”

Section: Introductionmentioning

confidence: 99%

Characterization of bis(2,2'-bipyridine) and bis(1,10-phenanthroline) derivatives of molybdenum and tungsten carbonyls. Crystal and molecular structure of cis-dicarbonylbis(2,2'-bipyridine)molybdenum(0)

Chisholm¹,

Connor²,

Huffman³

et al. 1984

Inorg. Chem.

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Diazoalkane complexes of tungsten from the condensation of hydrazido Complexes with Ketones

Cited by 54 publications

References 11 publications

Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

Synthesis of Tungsten (1-Pyridinio)imido Complexes: Facile N−N Bond Cleavage To Form Pyridine from Coordinated Dinitrogen¹

Characterization of bis(2,2'-bipyridine) and bis(1,10-phenanthroline) derivatives of molybdenum and tungsten carbonyls. Crystal and molecular structure of cis-dicarbonylbis(2,2'-bipyridine)molybdenum(0)

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Diazoalkane complexes of tungsten from the condensation of hydrazido Complexes with Ketones

Cited by 54 publications

References 11 publications

Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen

Synthesis of Tungsten (1-Pyridinio)imido Complexes: Facile N−N Bond Cleavage To Form Pyridine from Coordinated Dinitrogen1

Characterization of bis(2,2'-bipyridine) and bis(1,10-phenanthroline) derivatives of molybdenum and tungsten carbonyls. Crystal and molecular structure of cis-dicarbonylbis(2,2'-bipyridine)molybdenum(0)

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Synthesis of Tungsten (1-Pyridinio)imido Complexes: Facile N−N Bond Cleavage To Form Pyridine from Coordinated Dinitrogen¹