2-Diphenylphosphino-2′-hydroxybiphenyl-based P-ligands and their platinum(II) complexes

Keglevich, György; Kerényi, Andrea; Szelke, H.; Ludányi, Krisztina; Körtvélyesi, Tamás

doi:10.1016/j.jorganchem.2006.08.080

Cited by 16 publications

(6 citation statements)

References 17 publications

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“…Earlier studies [5,6,20,22,23,25] well demonstrated the selective formation of the corresponding cis-PtP 2 Cl 2 complexes, only in the case of considerable steric hindrance was the trans-PtP 2 Cl 2 species formed as the exclusive product [20,24]. This is in full agreement with the thesis of Pringle et al that in solution the cis-PtP 2 Cl 2 complexes are generally more stable than the corresponding trans species.…”

Section: Resultssupporting

confidence: 85%

A new family of platinum(II) complexes incorporating five‐ and six‐membered cyclic phosphine ligands

Kerényi

Kovács

Körtvélyesi

et al. 2010

Heteroatom Chemistry

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Section: Resultssupporting

confidence: 85%

A new family of platinum(II) complexes incorporating five‐ and six‐membered cyclic phosphine ligands

Kerényi

Kovács

Körtvélyesi

et al. 2010

Heteroatom Chemistry

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“…(3)], providing alcohol 13 in 69 % isolated yield. [38,39] Additional transformations involving the versatile CÀB bond that tolerate the protected phosphine to access complex phosphines are currently underway.…”

Section: Tertiaryphosphineshaveplayedaprominentroleinthefieldmentioning

confidence: 99%

Phosphine‐Directed CH Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters

et al. 2014

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Ambiphilic ligands have received considerable attention over the last two decades due to their unique reactivity as organocatalysts and ligands. The iridium-catalyzed CÀH borylation of phosphines is described in which the phosphine is used as a directing group to provide selective formation of arylboronate esters with unique scaffolds of ambiphilic compounds. A variety of aryl and benzylic phosphines were subjected to the reaction conditions, selectively providing stable, isolable boronate esters upon protection of the phosphine as the borane complex. After purification, the phosphine-substituted boronate esters could be deprotected and isolated in pure form.

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“…The main focus was on 6 H ‐dibenzo‐ and 6 H ‐dinaphtho[c,e][1,2]oxaphosphinines, which not only provided access to various achiral and chiral ligands and their use in homogeneous catalysis but also underwent ring opening reactions to O‐functionalized 1,1′‐biarylphosphane ligands. [5a], Whereas binaphthyl compounds with OR and PR 2 substituents in 2‐ and 2′‐position are configuratively stable, the barriers for the axial rotation of o , o ′‐biphenyl‐O,P ligands are too low to prevent atropisomerization . This raises the question whether the steric hindrance to rotation around the aryl–aryl‐axis might already be sufficient for o , o ′‐substituted 1‐phenylnaphthyl‐O,P compounds to suppress atropisomerization and to open the way to a diastereoselective ring‐opening of benzo‐naphtho‐anellated 6 H ‐1,2‐oxaphosphinines or to kinetic resolution by O‐substitution with a chiral reagent.…”

Section: Introductionmentioning

confidence: 99%

Benzo/Naphtho‐Anellated Dihydro‐1,2‐oxaphosphinines and Ring‐Opening to P‐Tertiary 2‐Phosphanyl‐1,1′‐biaryl‐2‐ol Derivatives – Syntheses and Structures

et al. 2017

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Reaction of naphthylphenol 1a and phenylnaphthol 1b, respectively, with PCl 3 in the presence of ZnCl 2 gave mixed benzo-and naphtho-anellated 6-chloro-6H-1,2-oxaphosphinines 2a and 2b. Treatment with equimolar amounts of tBuLi led to 6-tBu-substituted mixed-anellated oxaphosphinines 3a and 3b, respectively, and subsequent P-O-ring cleavage with methyllithium and quenching with ClSiMe 3 to 2-trimethylsilyloxy-biarylphosphanes 4a and 4b. NMR spectra indicated two data sets for 4a but only one for 4b, indicating higher diastereoselectivity in the ring opening of the 1,2-oxaphos-[a] Scheme 2. Synthesis of 1-di-o-anisylphosphanylphenyl-naphthyl-silyl ether 5b and -camphanic acid ester 6b. 3582 dd, 3 J = 8.5, 3 J PH = 6.8 Hz, 1 H, 3′-H, A, B), 7.86 (superimp. d br, 3 J = 7.7 Hz, 1 H, 8′-H, A, B) ppm; assigned tentatively by comparison with 1a MOM and other related compounds (Table S1). 31 P{ 1 H} NMR (CDCl 3 ): δ = -20.5, -24.2 (integrals A:B 63:37) ppm. rac-1-(2-tert-Butylmethylphosphanyl)phenyl-naphth-2-yl Trimethylsilyl Ether (4b) via 5-tert-Butyl-5H-benzo[c]-naphtho-[1,2-e]-1,2-oxaphosphinine (3b): i) A solution of tBuLi in pentane(2.5 mL, 1.5 M, 3.75 mmol) was added dropwise at -90°C to a solution of 2b (1.06 g, 3.72 mmol mmol) in toluene (20 mL). The mixture was warmed slowly to room temperature with stirring overnight to give a pale brown solution. NMR monitoring indicated quantitative conversion of 2b to 3b. 1 H NMR (CDCl 3 ): δ = 0.90 (d, 3 J PH = 13.5 Hz, 9 H,

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2-Diphenylphosphino-2′-hydroxybiphenyl-based P-ligands and their platinum(II) complexes

Cited by 16 publications

References 17 publications

A new family of platinum(II) complexes incorporating five‐ and six‐membered cyclic phosphine ligands

A new family of platinum(II) complexes incorporating five‐ and six‐membered cyclic phosphine ligands

Phosphine‐Directed CH Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters

Benzo/Naphtho‐Anellated Dihydro‐1,2‐oxaphosphinines and Ring‐Opening to P‐Tertiary 2‐Phosphanyl‐1,1′‐biaryl‐2‐ol Derivatives – Syntheses and Structures

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