Bis(phosphinomethyl)phenylamines and bis(phosphinomethyl)sulfides and their reaction with d8-platinum group precursors

Stickel, Marc; Maichle‐Moessmer, Caecilia; Wesemann, Lars; Mayer, Hermann A.

doi:10.1016/j.poly.2012.07.083

Cited by 7 publications

(9 citation statements)

References 41 publications

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“…Bond distance and interligand angles describing the coordination spheres in 2-4 do not significantly depart from the values reported for [MCl 2 {RN(CH 2 PPh 2 ) 2 -k 2 P,P'}] (M/R = Et/Ni, [29] Pd/Ph [30] and Pt/Ph [31] ). As expected, the MÀ P and MÀ Cl distances are shorter in 2 than in the Pd and Pt(II) complexes, which in turn show similar values.…”

Section: Synthesis and Structures Of Group 10 Metal Complexescontrasting

confidence: 55%

“…NMR (399.95 MHz, CDCl 3 ): δ = 3.78 (vt, J' = 1.9 Hz, 2 H, C 5 H 4 ),3.83 (vt, J' = 1.9 Hz, 2 H, C 5 H 4 ), 3.88 (d, 2 J PH = 2.0 Hz, 4 H, CH 2 ), 4.12 (s, 5 H, C 5 H 5 ), 7.29-7.33 (m, 12 H, PPh 2 ), 7.36-7.43(m, 8 H, PPh 2 ) ppm 31. P { 1 H} NMR (161.05 MHz, CDCl 3 ): δ = À 25.3 (s) ppm.…”

mentioning

confidence: 99%

“…NMR (399.95 MHz, CDCl 3 ): δ = 1.26 (t, J = 7.1 Hz, 3 H, CH 2 CH 3 of AcOEt), 1.42 (s, 6H, C 6 H 12 ), 2.04 (s, 3 H, CH 3 CO of AcOEt), 3.39 (vt, J' = 1.9 Hz, 4 H, C 5 H 4 ),3.79 (vt, J' = 1.8 Hz, 4 H, C 5 H 4 ),3.95 (br s, 8 H, CH 2 PPh 2 ), 4.02 (s, 10 H, C 5 H 5 ), 4.12 (q, J = 7.2 Hz, 2 H, CH 2 CH 3 of AcOEt), 7.11-7.19 (m, 32 H, PPh 2 ), 7.33-7.39 (m, 8 H, PPh 2 ) ppm 31. P { 1 H} NMR (161.90 MHz, CDCl 3 ): δ = À 14.9 (br s, PPh 2 ), À 143.6 (septet, PF = 713 Hz, PF 6 ) ppm.…”

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confidence: 99%

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Synthesis, Coordination and Electrochemistry of a Ferrocenyl‐Tagged Aminobisphosphane Ligand

2021

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Introducing a ferrocene moiety into a molecule results in the incorporation of a metal center and a redox active moiety. This contribution describes the synthesis of FcN(CH 2 PPh 2 ) 2 (1; Fc = ferrocenyl), a ferrocene analog of the widely studied bisphosphane pincer ligands, RN(CH 2 PPh 2 ) 2 . Compound 1 was studied as a ligand in complexes of Group 10 and 11 metal ions. The following compounds were synthesized and characterized using a combination of spectroscopic methods and single-crystal X-ray diffraction analysis: the square planar complexes [MX 2 (1-k 2 P,P')] (M/X = Ni/Cl, Pd/Cl, Pd/Br, Pd/I and Pt/ Cl) and the tetrahedral complexes [M(1-k 2 P,P') 2 ]X (M/X = Cu/PF 6 , Ag/SbF 6 and Au/SbF 6 ). Furthermore, a pair of open and cyclic digold(I) complexes containing bis-phosphane 1 as a P,Pbridging ligand, viz. [(μ(P,P')-1)(AuCl) 2 ] and [(μ(P,P')-1) 2 Au 2 ][SbF 6 ] 2 , were isolated. Ligand 1, the corresponding phosphane selenide 1-Se and all complexes (except for the poorly soluble [(μ(P,P')-1) 2 Au 2 ][SbF 6 ] and unstable [Ag(1k 2 P,P') 2 ][SbF 6 ]) were further analyzed by cyclic voltammetry.

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Section: Synthesis and Structures Of Group 10 Metal Complexescontrasting

confidence: 55%

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confidence: 99%

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Synthesis, Coordination and Electrochemistry of a Ferrocenyl‐Tagged Aminobisphosphane Ligand

2021

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“…Also, the observed wavenumber is larger than would be expected for a carbonyl band if all three phosphine groups were coordinated to only one rhodium(I) center 51. The trans cyanido platinum complex 4b shows one strong IR absorption at ν(CN) = 2127 cm –1 , which is well comparable to systems with mutually trans‐positioned cyanides, like in {Pt 2 [bis(dicyclohexylphosphino)methane] 2 (CN) 4 } [ν(CN) = 2125 cm –1 ],52 and which clearly differs from systems with mutually cis‐coordinated cyanido ligands, as in {Pt[bis(diphenylphosphinomethyl)‐phenylamine](CN) 2 } [ν(CN) = 2145 cm –1 ] 26…”

Section: Resultsmentioning

confidence: 85%

Trimeric Cage Complexes of Platinum Group and Coin Metals

2013

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“…[18] The PtÀ P and PtÀ Cl bond distances in 5 are in the range expected. [19] The six-membered metallacycles in 4 and 5 adopt twisted boat conformation to minimize the steric interaction between benzhydryl side arms and PPh 2 groups. Both the complexes by ChemistrySelect virtue of bulkiness showed CÀ H⋅⋅⋅π intramolecular interactions between the methylene hydrogen of À NCH 2 PPh 2 groups with the ipso carbon of one of the phenyl rings of the benzhydryl groups (H34 A⋅⋅⋅C9 2.551 Å, H35 A⋅⋅⋅C28 2.604 Å in 4, H34 A⋅⋅⋅C9 2.789 Å, and H35B⋅⋅⋅C28 2.465 Å in 5).…”

Section: Synthesis Of Pd II and Pt Ii Complexes 4-6mentioning

confidence: 99%

Transition Metal Complexes of 2,6‐Dibenzhydryl Derived Bisphosphine: Synthesis, Structural Studies and Palladium Complex Promoted Suzuki‐Miyaura Reactions

et al. 2022

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Transition metal chemistry of [Ar*N(CH 2 PPh 2 ) 2 ] (1) derived from the sterically demanding backbone 2,6-dibenzhydryl-4-methylphenyl core is described. The reactions of 1 with 30 % aq. H 2 O 2 and S 8 afforded bischalcogenides [Ar*N(CH 2 P(O)Ph 2 ) 2 ] (2) and [Ar*N(CH 2 P(S)Ph 2 ) 2 ] (3), respectively. Treatment of 1 with [M(COD)Cl 2 ] (M = Pd, Pt) in 1 : 1 molar ratios produced chelate complexes cis-[MCl 2 {Ar*N(CH 2 PPh 2 ) 2 }-k 2 -P,P] (4, M = Pd; 5, M = Pt), whereas similar reaction between 1 and [Pd(η 3 -C 3 H 5 )Cl] 2 afforded dinuclear complex [{Pd(η 3 -C 3 H 5 )Cl} 2 {Ar*N(CH 2 PPh 2 ) 2 }k 1 -P,P] (6). The reaction of 1 with [Ru(η 5 -C 5 H 5 )Cl(PPh 3 ) 2 ] in 1 : 1 ratio yielded [{Ru(η 5 -C 5 H 5 )Cl}{Ar*N(CH 2 PPh 2 ) 2 }-k 2 -P,P] (7). Treatment of 1 with [M(C 5 H 11 N) 2 (CO) 4 ] (M = Mo, W) in 1 : 1 molar ratios afforded cis-[M(CO) 4 {Ar*N(CH 2 PPh 2 ) 2 }-k 2 -P,P] (8, M = Mo; 9, M = W). The reaction of 1 with copper(I) halides in 1 : 1 molar ratios produced [Cu(μ 2 -X)] 2 dinuclear complexes [{Cu(μ 2 -X)} 2 {Ar*N(CH 2 PPh 2 ) 2 } 2 -k 2 -P,P}] [10, X = Cl; 11, X = Br; and 12, X = I]. Most of these compounds show various CÀ H⋅⋅⋅π interactions. Bischalcogenides 2 and 3 showed intramolecular hydrogen bonding type interactions, CÀ H⋅⋅⋅O (2.554 Å) and CÀ H⋅⋅⋅S (2.825 Å) between the methylene hydrogens of -NCH 2 PPh 2 groups with O or S atoms, which was also evinced by QTAIM and NCI analysis. Bisphosphine 1 was found to be very effective in palladium catalyzed Suzuki-Miyaura couplings of aryl chlorides with aryl boronic acids.

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Bis(phosphinomethyl)phenylamines and bis(phosphinomethyl)sulfides and their reaction with d8-platinum group precursors

Cited by 7 publications

References 41 publications

Synthesis, Coordination and Electrochemistry of a Ferrocenyl‐Tagged Aminobisphosphane Ligand

Synthesis, Coordination and Electrochemistry of a Ferrocenyl‐Tagged Aminobisphosphane Ligand

Trimeric Cage Complexes of Platinum Group and Coin Metals

Transition Metal Complexes of 2,6‐Dibenzhydryl Derived Bisphosphine: Synthesis, Structural Studies and Palladium Complex Promoted Suzuki‐Miyaura Reactions

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