Kinetic study on the reaction of cis-dioxo-(N-(5-X-salicylidene)-2-aminobenzenethiolato) molybdenum(VI) with ethyldiphenylphosphine

Topich, J.; Lyon, James T.

doi:10.1016/s0277-5387(00)84713-0

Cited by 16 publications

(8 citation statements)

References 19 publications

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“…Similar observations have previously been made with other ligands, including other tridentate Schiff base ligands, such as those obtained by condensation of substituted salicylaldehydes with ortho ‐aminobenzenethiol,17 substituted thiophenolate,44 substituted dithiolenes,45 and salan‐type ligands 21,41. A particularly pronounced effect of the NO 2 substituent was also observed by Britovsek and Gibson et al with dioxomolybdenum complexes with para ‐substituted salan‐type ligands 21…”

Section: Resultssupporting

confidence: 85%

“…In addition, dioxo‐molybdenum complexes with ligands of higher denticity and mixed donor sets have shown promise (Figure 1). Commonly studied tridentate ligands include facially coordinating hydrotris(pyrazolyl)borates (e.g., Tp*, 1 14–16) and meridionally coordinating Schiff base derivatives (e.g., ssp, 2 17 and tsc, 3 18,19). Whereas tridentate ligands can occupy only three of the four available coordination sites on the cis ‐MoO 2 center, tetradentate ligands, including tripodal (N3O, 4 20) or linear (salan21,22) ligands ( 5 ) form coordinatively saturated complexes.…”

Section: Introductionmentioning

confidence: 99%

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Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Zhao

Yang

Tang

et al. 2015

Chemistry A European J

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Rh(II)-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3+n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

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Section: Resultssupporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Zhao

Yang

Tang

et al. 2015

Chemistry A European J

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“…In addition, if EWGs lower the energy of the transition state by ameliorating negative charge build-up, they give rise to faster reaction rates. Similar observations have previously been made with other ligands, including other tridentate Schiff base ligands, such as those obtained by condensation of substituted salicylaldehydes with ortho-aminobenzenethiol, [17] substituted thiophenolate, [44] substituted dithiolenes, [45] and salan-type ligands. [21,41] A particularly pronounced effect of the NO 2 substituent was also observed by Britovsek and Gibson et al with dioxomolybdenum complexes with para-substituted salan-type ligands.…”

Section: Catalytic Oxygen Atom Transfer Activitysupporting

confidence: 86%

“…Commonly studied tridentate ligands include facially coordinating hydrotris(pyrazolyl)borates (e.g., Tp*, 1 [14][15][16] ) and meridionally coordinating Schiff base derivatives (e.g., ssp, 2 [17] and tsc, 3 [18,19] ). Whereas tridentate ligands can occupy only three of the four available coordination sites on the cisMoO 2 center, tetradentate ligands, including tripodal (N3O, 4 [20] ) or linear (salan [21,22] ) ligands (5) form coordinatively saturated complexes.…”

Section: Introductionmentioning

confidence: 99%

Electronic Fine‐Tuning of Oxygen Atom Transfer Reactivity of cis‐Dioxomolybdenum(VI) Complexes with Thiosemicarbazone Ligands

et al. 2015

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A series of six cis‐dioxomolybdenum(VI) complexes with thiosemicarbazone ligands was synthesized and characterized. The ligands were obtained by reacting ethyl thiosemicarbazide with salicylaldehydes substituted with a selection of electron‐withdrawing and electron‐donating groups. The crystal structures, IR, NMR spectroscopic data and oxygen atom transfer activities of the complexes revealed that the electronic effects of the substituents located in the para‐position of the phenolate donor are transmitted through to the molybdenum center, as reflected by linear relationships between Hammett constants and key properties of the complexes, including the molybdenum–phenolate bond lengths and the coordination shift of the imine proton resonance. Compared with the unsubstituted catalyst, electron‐withdrawing substituents increase the rate of oxygen atom transfer from dimethyl sulfoxide to triphenylphosphine, whereas electron‐donating groups have the opposite effect. The highest rate enhancement was achieved through the introduction of a strongly electron‐withdrawing NO2 substituent in the p‐position of the phenolate donor.

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“…for the more reactive Ph2PEt with a series of MoO2 complexes containing tridentate salicylaldimino ligands with one coordinated thiolate (40).…”

Section: Reactivities Of Complexes 15 and 16mentioning

confidence: 99%

Mononuclear active sites of molybdoenzymes: chemical approaches to structure and reactivity

Holm¹,

Berg²

1984

Pure and Applied Chemistry

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-One of two general classes of molybdoenzymes contains mononuclear catalytic sites and effects oxidation or reduction of substrate x/x0 by oxygen atom transfer: X + (0)XO. The reaction LMoO2 + X -3LMo0 + X0 is well established in synthetic systems, and is fre- In a synthetic approach to these sites, the ligand pyridine-2,6-biswas prepared. Reaction with MoO 2(acac)2 afforded the 5-coordinate trigonal bipyramidal complex Mo02(L-NS2), which was converted to MoO-

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Kinetic study on the reaction of cis-dioxo-(N-(5-X-salicylidene)-2-aminobenzenethiolato) molybdenum(VI) with ethyldiphenylphosphine

Cited by 16 publications

References 19 publications

Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Electronic Fine‐Tuning of Oxygen Atom Transfer Reactivity of cis‐Dioxomolybdenum(VI) Complexes with Thiosemicarbazone Ligands

Mononuclear active sites of molybdoenzymes: chemical approaches to structure and reactivity

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Kinetic study on the reaction of cis-dioxo-(N-(5-X-salicylidene)-2-aminobenzenethiolato) molybdenum(VI) with ethyldiphenylphosphine

Cited by 16 publications

References 19 publications

RhII‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

RhII‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Electronic Fine‐Tuning of Oxygen Atom Transfer Reactivity of cis‐Dioxomolybdenum(VI) Complexes with Thiosemicarbazone Ligands

Mononuclear active sites of molybdoenzymes: chemical approaches to structure and reactivity

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Product

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Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles

Rh^II‐Catalyzed [3+2] Cycloaddition of 2 H‐Azirines with N‐Sulfonyl‐1,2,3‐Triazoles