Synthesis and X-ray structural characterization of the triphenylphosphine derivative of the closo-dodecaborate anion, closo-[B12H11P(C6H5)3][N(n-C4H9)4]

Bernard, Rémy; Cornu, David; Luneau, Dominique; Naoufal, Daoud; Scharff, J.P.; Miele, Philippe

doi:10.1016/j.jorganchem.2005.01.045

Cited by 21 publications

(14 citation statements)

References 28 publications

(29 reference statements)

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“…The salt of monophosphonium, [N(n-Bu) 4 ][(PPh 3 )B 12 H 11 ], was obtained in good yield and purity by Cornu and co. 9 The starting material was the monoiodo-dodecaborate, [B 12 H 11 I] 2À , that reacts with the palladium complex [Pd(PPh 3 ) 4 ] in the presence of Na 2 CO 3 as a base in THF.…”

Section: C B Cluster -P Bond Formation On Dodecaboratementioning

confidence: 99%

Methods to produce B–C, B–P, B–N and B–S bonds in boron clusters

et al. 2013

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Boranes, heteroboranes and metallacarboranes, all named as boron clusters, offer an alternative to typical organic molecules or organic molecular materials. Carbon and boron share the important property of self-catenation thus these elements can produce individually large and sophisticated molecules. Boron clusters and organic molecules display electronic, physical, chemical and geometrical characteristics manifestly different. These differences highlight the complementarity of organic molecules and boron clusters, and therefore the feasibility or necessity to produce hybrid molecules incorporating both types of fragments. To join these two types of fragments, or alternatively these two types of molecular compounds, tools are needed. In this review the current methods of producing boron clusters with carbon, B-C, nitrogen, B-N, phosphorus, B-P and sulphur bonds, B-S, are indicated. As there are many existing borane clusters of different sizes, heteroboranes and metallacarboranes, the revision of methods to generate the B-C, B-P, B-S, and B-N bonds has been restricted to the most widely used boron clusters; [B12H12](2-), dianionic and an example of a borane, 1,2-C2B10H12, neutral and an example of a heteroborane, and [Co(C2B9H11)2](-), monoanionic and an example of a metallacarborane.

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Section: C B Cluster -P Bond Formation On Dodecaboratementioning

confidence: 99%

Methods to produce B–C, B–P, B–N and B–S bonds in boron clusters

et al. 2013

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“…The precipitate was washed with a mixture water/ethanol (1 : 1). Further recrystallization in DMF yielded 0.201 g (0.6 mmol, 20%) of (E,E)-4-(2-(4-(2-(4-cyanophenyl)ethenyl)phenyl)ethenyl)benzaldehyde (9). In a third step, 0.107 g (0.32 mmol) of 9 and 0.262 g (6.54 mmol) of 1 were dissolved in 20 mL of DMF.…”

Section: Synthesis Of [Nc-c 6 H 4 -Ch=ch-c 6 H 4 -Ch=ch-c 6 H 4 -C(h)...mentioning

confidence: 99%

“…The dodecahydro-closo-dodecaborate dianion, [B 12 H 12 ] 2− , possesses the unique structure of a regular icosahedron and unique properties, such as high thermal stability, remarkable chemical and hydrolytical stability, and low toxicity. Since the isolation of closo-[B 12 H 12 ] 2− was first reported in 1960, 1 several routes to substituted closo-dodecaborate anions were envisaged via the formation of boron-nitrogen, 2,3 -oxygen, 4,- 6 -sulfur, 7 -halogen, 8 -phosphorus 9 or -carbon 10,11 bonds. Their intrinsic properties make B 12 -derivatives suitable for various possible applications, ranging from biomedical ones like boron neutron capture therapy (BNCT), a method for the treatment of cancer based upon the interaction of 10 B atoms and thermal neutrons, 12 to the selective extraction of radionuclides from nuclear wastes arising from the PUREX process.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and optical properties of π-conjugated systems incorporating closo-dodecaborate clusters: new potential candidates for two-photon absorption processes

et al. 2005

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Non-centrosymmetric pi-conjugated systems incorporating closo-dodecaborate clusters, [NC-C6H4-C(H=N(H)-B12H11]-(2), [NC-C6H4-C(H)=C(H)-C(6)H(4)-C(H)=N(H)-B12H11]-(3), and [NC-C6H4-C(H)=C(H)-C6H4-C(H)=C(H)-C6H4-C(H)=N(H)-B12H11]-(4) have been synthesized by reaction of the monoamino derivative of B12, [B12H11NH3]-(1), with various arylaldehydes, R-C6H4-CHO. These Schiff base-like compounds were fully characterized by multinuclear NMR spectroscopy and mass spectrometry. In order to evaluate these boron rich pi-systems as potential materials for two-photon absorption (TPA) processes, UV linear absorption curves were recorded for 3 and 4, and comparatively studied with those of the boron-free pi-systems NC-C6H4-C(H)=N-CH3(5) and NC-C6H4-C(H)=C(H)-C6H4-C(H)=N-CH3(6). The donor effect of the boron cluster was evidenced by a shift to the lower energy of the absorption band in the spectra of systems incorporating B12. The two photon absorption (TPA) spectrum of compound , obtained by the up-conversion method, shows a resonance at 720 nm with a cross-section sigma(TPA) of 35 x 10(-50) cm(4) s photon(-1) molecule(-1). This value suggests the potential of B12 clusters to be used as new donor groups for the synthesis of non-linear materials.

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“…A very useful synthetic approach to functionalized { closo ‐B 12 } clusters is the palladium‐catalyzed replacement of an iodine substituent, which can be easily introduced by an electrophilic reaction, against a functional group 5. Examples for cross‐coupling reactions are the syntheses of derivatives with a substituent that is bonded by carbon to a cluster boron atom following either a Kumada‐type6or a Negishi‐type protocol,7 and the preparation of[ n Bu 4 N][Ph 3 P‐ closo ‐B 12 H 11 ] 8…”

Section: Introductionmentioning

confidence: 99%

Cesium and Tetrabutylammonium Salt of the Ethynyl‐closo‐dodecaborate Dianion

Himmelspach

Finze

Vöge

et al. 2012

Zeitschrift anorg allge chemie

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Salts of the ethynyl-closo-dodecaborate dianion [HCϵCcloso-B 12 H 11 ] 2-(1) were synthesized by a microwave-assisted palladium-catalyzed cross-coupling reaction starting from the iodinated cluster [I-closo-B 12 H 11 ] 2and Me 3 SiCϵCMgBr. The dianion was characterized in its [nBu 4 N] + and Cs + salt by multi-NMR and vibrational spectroscopy as well as by (-)-MALDI mass spectrometry. A crystal of [nBu 4 N] 2 [HCϵC-closo-B 12 H 11 ] was studied by X-ray dif-* Prof. Dr. M. Finze

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Synthesis and X-ray structural characterization of the triphenylphosphine derivative of the closo-dodecaborate anion, closo-[B12H11P(C6H5)3][N(n-C4H9)4]

Cited by 21 publications

References 28 publications

Methods to produce B–C, B–P, B–N and B–S bonds in boron clusters

Methods to produce B–C, B–P, B–N and B–S bonds in boron clusters

Synthesis, characterization and optical properties of π-conjugated systems incorporating closo-dodecaborate clusters: new potential candidates for two-photon absorption processes

Cesium and Tetrabutylammonium Salt of the Ethynyl‐closo‐dodecaborate Dianion

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