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Vicente, Jos�; Abad, Jos�-Antonio; Bergs, Ralph; Jones, Peter G.; Bautista, Delia

doi:10.1039/dt9950004131

Cited by 12 publications

(31 citation statements)

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“…In all cases this band is shifted to the higher wavenumber region with respect to that in the corresponding free ylide between 77 (2a′) and 106 (4) cm -1 . We have previously attributed a similar blue-shift found in many silver (I), 27,28 gold (I), 26,27,29-39 gold(III), 26,27,[29][30][31] and palladium (II) [40][41][42][43] ylide complexes to the reinforcement of the p(π)O f p(π)C bond component caused by the nucleophilic attack of the ylide at the metal center, and the same argument could be also used in this case. We have previously shown that in complexes containing carbonyl-stabilized phosphorus ylide moieties there is a close dependence of the position of the CO band on the electronegativity of the substituents attached to the ylide carbon atom.…”

Section: Synthesis Complexes [Mclmentioning

confidence: 59%

Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

et al. 1999

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Carbonyl-stabilized phosphorus ylides R3PCHC(O)R‘ (R = Ph, Tol-p; R‘ = OEt, OMe, NMe2) react with the 1,5-cyclooctadiene complexes [MCl2(cod)] (M = Pt, Pd; cod = C8H12 = 1,5-cyclooctadiene) to give the monomeric cyclooctenyl complexes [MCl2{C8H12{CH(PR3)C(O)R‘}}]. The ylides attack in an exo fashion to give complexes which can be regarded as metalated phosphonium salts. Reactions involving the replacement of one or both chloro ligands with a neutral ligand are discussed. The crystal structures of complexes [PtCl2{C8H12{CH(PPh3)CO2Me}}] and [Pt{C8H12{CH(PPh3)CO2Me}}(py)2](CF3SO3)2 are reported.

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Section: Synthesis Complexes [Mclmentioning

confidence: 59%

Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

et al. 1999

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“…3 We have reported the syntheses of acetonyl derivatives of gold(III) and thallium(III) through two different C-H bond-activation processes [3][4][5][6][7][8][9][10][11] and a carbacyclic ketonylaryl palladium(II) complex by proton abstraction from a 2-acetylarylpalladium(II) complex with a phosphorus ylide or NaOMe. 12 The number of acetonyl complexes of palladium(II) and platinum(II) is rather limited. So far, only monoac-etonyl complexes have been reported, including the cationic complex [Pt{CH 2 C(O)Me}(PPh 3 ) 3 ]BF 4 13 and a few neutral derivatives of the type [M{CH 2 C(O)Me}XL 2 ] (M ) Pd, Pt) for which the anionic X ligand can be Cl, [14][15][16][17][18] Ph, 14,19 Me, 19,20 or cyclohexen-1-yl 21 while the neutral L ligands are always tertiary phosphines (PEt 3 , 14,19 PMePh 2 , PEtPh 2 , 15 PPh 3 , 13,16,17,19 or L 2 ) dppe 20,21 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Ketonyl Palladium(II) and Platinum(II) Complexes with Nitrogen-Donor Ligands. Crystal Structure of [Pt{CH₂C(O)Me}₂(bpy)]

et al. 1998

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Complexes [MCl2L2] (M = Pd, Pt; L2 = 2,2‘-bipyridine (bpy) or Me2N(CH2)2NMe2 (tmeda)) react with ketones MeC(O)R (R = Me, Et) in the presence of bases (Ag2O or M‘OH (M‘ = Na, K)) to give the new types of ketonyl palladium(II) and platinum(II) complexes [M{CH2C(O)R}ClL2] (M = Pd, L2 = N,N,N‘,N‘-tetramethylethylenediamine = tmeda; M = Pt, L2 = 2,2‘-bipyridine = bpy) and [Pt{CH2C(O)R}2L2] (R = Me, Et, L2 = bpy). Oxidative addition of chloroacetone on [Pt(dba)2] in the presence of bpy also yields [Pt{CH2C(O)R}ClL2]. [Pd{CH2C(O)Me}Cl(tmeda)] reacts with PhNHNH2 in the presence of TlOTf (OTf = CF3SO3) to give the cyclometalated complex [Pd{CH2C(Me)NNH(Ph)}(tmeda)]OTf. The crystal structure of [Pt{CH2C(O)Me}2(bpy)] has been determined. The platinum atom is in a distorted square-planar environment. The strong trans influence of the acetonyl ligand promotes the lengthening of both Pt−N bonds (2.082(3) and 2.091(3) Å) with concomitant narrowing of the NPtN bond angle (78.89(13)°).

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“…35,36 We are currently investigating the synthesis and reactivity of (2,3,4-trimethoxyaryl)palladium complexes bearing different substituents at the 6 position. 1, [37][38][39][40][41][42][43][44] Given the nature of the functional substituents attached to the aryl ring, which are often incompatible with the use of lithium or Grignard reagents, such complexes have been synthesized by a route, widely exploited by us, using the corresponding diarylmercurials as transmetalating agents. 45 Starting from these arylpalladium compounds, we have recently prepared indenones, indenols, 1,44 benzofulvenes, 39 and spirocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Assisted Formation of Carbon−Carbon Bonds. 7.¹ Reactions of (2,3,4-Trimethoxy-6-X-phenyl)palladium Complexes with Alkynes (X = C(O)NHBu^t) and Isocyanides (X = C(O)NHBu^t, C(O)Me, CHO): Crystal and Molecular Structures of [Pd{C₆H{C(O)NHBu^t}-6-(OMe)₃-2,3,4}(bpy)](CF₃SO₃), [Pd{C(CO₂Me)C(CO₂Me)C₆H{C(O)NHBu^t}-6-(OMe)₃-2,3,4)}- Cl(PPh₃)], [Pd{C(NXy)C<

et al. 1997

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The mercuriation of 3,4,5-trimethoxy(N-tert-butylcarbamoyl)benzene with mercury(II) acetate and subsequent reaction with KCl leads to the formation of [Hg{C 6 The reaction of 2 with [PdCl 2 (MeCN) 2 ] and 2,2′-bipyridine (bpy) affords [Pd(C 6 H{C(O)NHBu t }-6-(OMe) 3 -2,3,4)Cl(bpy)] (3), which reacts with Tl(CF 3 SO 3 ) giving [Pd-{C 6 H{C(O)NHBu t }}(bpy)](CF 3 SO 3 ) (4). Complex 2 reacts with [PdCl 2 (MeCN) 2 ] and acetylenes RCtCR to give metallic palladium and the spirocyclic compound 10-(N-tert-butylcarbamoyl)-6,7-dimethoxy-1,2,3,4-tetraphenylspiro[4.5]-1,3,6,9-decatetraen-8-one (5) when R ) Ph or the monoinserted palladium complex [Pd{C(CO 2 Me)dC(CO 2 Me)C 6 H{C(O)NHBu t }-6-(OMe) 3 -2,3,4}(µ-Cl)] 2 (6) when R ) CO 2 Me. By reaction of 6 with L (1:2) or PPh 3 and Tl(CF 3 SO 3 ) (1:4:2), the complexes [Pd{C(CO 2 Me)dC(CO 2 Me)C 6 H{C(O)NHBu t }-6-(OMe) 3 -2,3,4}Cl(L)] (L ) PPh 3 (7), CNXy (8) (Xy ) 2,6-dimethylphenyl)) or [Pd{C(CO 2 Me)dC(CO 2 Me)C 6 H{C(O)-NHBu t }-6-(OMe) 3 -2,3,4}(PPh 3 ) 2 ](CF 3 SO 3 ) (9) are obtained respectively. The reactions of 4 and of the related complexes [Pd{C 6 H{C(O)Me}-6-(OMe) 3 -2,3,4}(bpy)](CF 3 SO 3 ) (10) or [Pd-{C 6 H{C(O)H}-6-(OMe) 3 -2,3,4}(NCMe)(bpy)](CF 3 SO 3 ) (11) with CNXy have also been studied, the following compounds being isolated: [Pd{C(dNXy)C 6 H{C(O)NHBu t }-6-(OMe) 3 -2,3,4}-(bpy)](CF 3 SO 3 ) (12) [Pd{C 6 H{C(O)Me}-6-(OMe) 3 -2,3,4}(CNXy)(bpy)](CF 3 SO 3 ) (13), [Pd-{C 6 H{C(O)H}-6-(OMe) 3 -2,3,4}(CNXy)(bpy)](CF 3 SO 3 ) (14), and the ketenimine 2-(2,6dimethylphenyl)-1-(((2,6-dimethylphenyl)imino)methylene)-5,6,7-trimethoxy-3-oxoisoindoline (15). The structures of 4, 7, 12, and 15 have been determined by X-ray crystallography.

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Additions and corrections

Cited by 12 publications

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Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

Synthesis of New Ketonyl Palladium(II) and Platinum(II) Complexes with Nitrogen-Donor Ligands. Crystal Structure of [Pt{CH₂C(O)Me}₂(bpy)]

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Additions and corrections

Cited by 12 publications

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Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

Nucleophilic Attack of Carbonyl-Stabilized Phosphorus Ylides on 1,5-Cyclooctadiene Complexes of Palladium and Platinum

Synthesis of New Ketonyl Palladium(II) and Platinum(II) Complexes with Nitrogen-Donor Ligands. Crystal Structure of [Pt{CH2C(O)Me}2(bpy)]

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Synthesis of New Ketonyl Palladium(II) and Platinum(II) Complexes with Nitrogen-Donor Ligands. Crystal Structure of [Pt{CH₂C(O)Me}₂(bpy)]