Synthesis, Structure and Properties of Crowded Triarylphosphines

Sasaki, Shigeru; Yoshifuji, Masaaki

doi:10.2174/138527207779316507

Cited by 41 publications

(27 citation statements)

References 22 publications

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“…Moreover, the 13 C NMR spectrum of the former 4 recorded two singlet signals at d 16.3 and 17.0 ppm due to the presence of two methyl groups, while the latter compound 6 recorded one signal at d 41.5 ppm (J C,P ¼ 55.8 Hz) which is assigned to CH 2 -P group. Additionally, the 31 P NMR spectrum showed one singlet signal for each at upfield d À11.2 and À18.4 ppm for compounds 4 and 6, respectively, which are in accordance with phosphorus (V) derivatives [21].…”

Section: Resultssupporting

confidence: 59%

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Ali

2009

European Journal of Medicinal Chemistry

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Section: Resultssupporting

confidence: 59%

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Ali

2009

European Journal of Medicinal Chemistry

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“…Additionally, it provides the possibility to use different acetylenes, which makes this approach a facile one-step synthesis of various PAHs including five-membered rings. As a further advantage it is shown that readily available palladium catalysts in combination with well understood phosphine ligands [21] can be used.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Eversloh

Avlasevich

et al. 2011

Chemistry A European J

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We present a new and versatile one-step synthesis of a series of small molecular chromophores based on cyclopentannulated polycyclic aromatic hydrocarbons (PAH). Easily available pyrene, anthracene, and perylene bromides serve as starting materials for the reactions. The formation of the five-membered ring is achieved by the straightforward palladium(0)-catalyzed carbannulation with various substituted acetylenes. This approach is applicable either to single or multiple annulation procedures leading to hitherto inaccessible PAH topologies. According to the resulting products of the diverse reactions, a mechanistic explanation is proposed. UV/Vis absorption as well as cyclovoltammetric measurements were performed for characterization demonstrating the value of this annulation technique. Optical absorptions of up to 780 nm and absorption coefficients ranging from 8000 to 34,000 M(-1) cm(-1) were detected.

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“…10 Thus, the steric hindrance by the t-butyl groups on the aryl groups or side reactions of the bromo group such as debromination probably caused further decrease of the yield. On the other hand the conversion of 6 to the arylcopper reagent and the following reaction with chlorobis(2,4,6-triisopropylphenyl)phosphine 13 gave [4-bromo-2,6-bis(4-tertbutylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine (1). Downloaded by [University of New Mexico] at 23:59 26 November 2014 Triarylphosphine 1 was obtained as pale yellow prisms, and the 31 P NMR chemical shift (δ − 40.7) is lower than that of tris(2,4,6-triisopropylphenyl)phosphine (3) (δ -51.9) and close to the previously reported [2,6-bis(4-methylphenyl)-4-methylphenyl]bis(2,4,6-triisopropylphenyl)phosphine (5a) (δ -42.3), reflecting the substituent effect of the 2,6-diarylphenyl group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure of Sterically Crowded Triarylphosphine Bearing 4-Bromo-2,6-Bis(4-tert-Butylphenyl)Phenyl Group

Sasaki

Izawa

Yoshifuji

2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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A novel sterically crowded triarylphosphine bearing a 2, 6-diaryl-4-bromophenyl group, [4-bromo-2,6-bis(4-tert-butylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine (1), was synthesized. The X-ray crystallography revealed that the bond angles and lengths around the phosphorus atom (110.9 • , 1.846 Å) are comparable to those of tris(2,4,6-triisopropylphenyl)phosphine and its derivatives. Triarylphosphine 1 is reversibly oxidized to the radical cation at the potential close to that of the typical sterically crowded (bromoaryl)phosphine, (4-bromo-2,6-diisopropylphenyl)bis (2,4,6-triisopropylphenyl)phosphine, and exhibits the UV absorption at long wavelength (λ max 332 nm) characteristic of the sterically crowded triarylphosphines. Thus, triarylphosphine 1 can be regarded to be a promising candidate for the key synthetic intermediate or building block to the functional molecules bearing sterically crowded triarylphosphine moieties.

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Synthesis, Structure and Properties of Crowded Triarylphosphines

Cited by 41 publications

References 22 publications

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Synthesis and Structure of Sterically Crowded Triarylphosphine Bearing 4-Bromo-2,6-Bis(4-tert-Butylphenyl)Phenyl Group

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