Phosphinomethylation of [1′-(diphenylphosphino)ferrocenyl]-methylamines as a route to unsymmetric ferrocene diphosphine ligands

Bárta, Ondřej; Cı́sařová, Ivana; Štěpnička, Petr

doi:10.1016/j.jorganchem.2017.11.024

Cited by 8 publications

(3 citation statements)

References 38 publications

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“…Yield, % δ P , ppm Me 3C (THF) 77 [135,136] -17.2 (CDCl 3 ) Me CH 2 CH 2 CN 3C (THF) 86 [135,136] -15.3 (CDCl 3 ) Me 3C (THF) 67 [136] -Me 3C (THF) 43 [136] -16.8 (CDCl 3 ) H Me Me 3C (MeOH) 89 [137] -26.0 (C 6 D 6 ) H Me CH 2 CO 2 H 3C (EtOH) 85 [138] -H Me 3C (C 6 H 6 ) 86 [139] -26.6 H Me 3C (Et 2 O) (-) [140] -26.2 (CDCl 3 ) H Me 2C (MeOH) 93 [141] -21.3 (CDCl 3 ) H Me 2C (MeOH) 91 [142] -26.4 (CDCl 3 ) H Et Et 3C (neat) 80 [3] -27.8…”

Section: Phosphine Aldehyde Aminementioning

confidence: 99%

“…Entry R R' Yield, % δ P , ppm 55 [281] -28.1 (CDCl 3 ) (-)*** [142] -27.7 for Ph 2 PCH 2 -(CDCl 3 ) 32 [148] -34.8 (CDCl 3 ) Me 78 [282] -42.7 (C 7 H 8 ) Et 84 [283] -44.0 (CD 2 Cl 2 ) i-Pr 79 [283] -42.1 (CD 2 Cl 2 ) 81 [283] -41.6 (CD 2 Cl 2 ) 74 [148] -44.5 (CDCl 3 ) Et Me > 70, [284] 71, [285,286] 84 [263] -31.0 (CD 3 CN) Et n-Bu 47 [285] -32.2 (CD 3 CN) Et t-Bu 65 [287] -29.3 (C 6 D 5 Br) Et 84 [263] -33.0 (THF-d 8 )…”

Section: Entry R R' R"unclassified

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Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Moiseev¹,

James

2022

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: Phosphine Aldehyde Aminementioning

confidence: 99%

Section: Entry R R' R"unclassified

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Moiseev¹,

James

2022

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Early on, the synthesis of phosphanyl ferrocenes bearing an additional polar group R on the other ring of the ferrocene backbone (Scheme a) has been pursued by the Štěpnička group, with R being carboxyl group . This work was further extended to numerous carboxamides, amidosulfonates, and other compounds that can serve as hybrid ligands and/or synthetic building blocks …”

Section: Introductionmentioning

confidence: 99%

Highly Functionalized Brønsted Acidic/Lewis Basic Hybrid Ferrocene Ligands: Synthesis and Coordination Chemistry

et al. 2019

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A general challenging issue in the synthesis of hemilabile ferrocene ligands is the access to highly functionalized ferrocene starting materials. These can bear donor/acceptor atoms, additional functional and structuring spectator substituents, but the preparation of such species poses general synthetic difficulties. We report herein alternative synthetic routes to hybrid ferrocene donors such as tert-butylated phosphanylcarboxylic acids and their corresponding aldehydes. These hybrid ambiphilic species that combine Brønsted-acidic and [a]

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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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Phosphinomethylation of [1′-(diphenylphosphino)ferrocenyl]-methylamines as a route to unsymmetric ferrocene diphosphine ligands

Cited by 8 publications

References 38 publications

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Highly Functionalized Brønsted Acidic/Lewis Basic Hybrid Ferrocene Ligands: Synthesis and Coordination Chemistry

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

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Phosphinomethylation of [1′-(diphenylphosphino)ferrocenyl]-methylamines as a route to unsymmetric ferrocene diphosphine ligands

Cited by 8 publications

References 38 publications

Phospha-Mannich reactions of RPH2, R2PH, and R3P

Phospha-Mannich reactions of RPH2, R2PH, and R3P

Highly Functionalized Brønsted Acidic/Lewis Basic Hybrid Ferrocene Ligands: Synthesis and Coordination Chemistry

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

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Product

Resources

About

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P

Phospha-Mannich reactions of RPH₂, R₂PH, and R₃P