B(C6F5)3-catalyzed formation of B–P bonds by dehydrocoupling of phosphine–boranes

Denis, Jean‐Marc; Forintos, Henrietta; Szelke, H.; Toupet, Loı̈c; Pham, Thi‐Nhàn; Madec, Pierre‐Jean; Gaumont, Annie‐Claude

doi:10.1039/b206559b

Cited by 113 publications

(116 citation statements)

References 11 publications

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“…Only ab initio calculations concerning the structure have been performed. [2] Under standard conditions only the poly(phosphanylboranes) of the formulae [H 2 BPH 2 ] n [3] or [H 2 BPPhH] n…”

Section: Introductionmentioning

confidence: 99%

Lewis Base Stabilized Phosphanylborane

Schwan

Timoskin

Zabel

et al. 2006

Chemistry A European J

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The abstraction of the Lewis acid from [W(CO)(5)(PH(2)BH(2)NMe(3))] (1) by an excess of P(OMe(3))(3) leads to the quantitative formation of the first Lewis base stabilized monomeric parent compound of phosphanylborane [H(2)PBH(2)NMe(3)] 2. Density functional theory (DFT) calculations have shown a low energetic difference between the crystallographically determined antiperiplanar arrangement of the lone pair and the trimethylamine group relative to the P-B core and the synperiplanar conformation. Subsequent reactions with the main-group Lewis acid BH(3) as well as with an [Fe(CO)(4)] unit as a transition-metal Lewis acid led to the formation of [(BH(3))PH(2)BH(2)NMe(3)] (3), containing a central H(3)B-PH(2)-BH(2) unit, and [Fe(CO)(4)(PH(2)BH(2)NMe(3))] (4), respectively. In oxidation processes with O(2), Me(3)NO, elemental sulfur, and selenium, the boranylphosphine chalcogenides [H(2)P(Q)BH(2)NMe(3)] (Q = S 5 b; Se 5 c) as well as the novel boranyl phosphonic acid [(HO)(2)P(O)BH(2)NMe(3)] (6 a) are formed. All products have been characterized by spectroscopic as well as by single-crystal X-ray structure analysis.

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Section: Introductionmentioning

confidence: 99%

Lewis Base Stabilized Phosphanylborane

Schwan

Timoskin

Zabel

et al. 2006

Chemistry A European J

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“…1a and 2). The unsaturated compound 3a crystallised with two molecules in the asymmetric unit, while the saturated compound 3b crystallised with one [27]). The C-S distances of 1.7320 (13), 1.7335 (14)Å for 3a and 1.7327 (15)Å for 3b are clearly lengthened compared to related imidazole-2-thiones (1.686 (3)Å; 1.674 (4)Å), because of the loss of the partial double bond character [25]; a search of the Cambridge Database [28] revealed ca.…”

Section: Discussionmentioning

confidence: 99%

Sulfur and SeleniumActivation by Frustrated NHC/B(C₆F₅)₃ Lewis Pairs; Conformational Flexibility of Products

Holschumacher

Daniliuc

Jones

et al. 2011

Zeitschrift Für Naturforschung B

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Frustrated Lewis pairs consisting of N-heterocyclic carbenes (NHC) and the borane B(C 6 F 5 ) 3 react with elemental sulfur or selenium to give products of the type NHC-E-B(C 6 F 5 ) 3 , where E is S or Se. Three such products, two with sulfur and one with selenium, were characterized by X-ray diffraction and shown to exhibit considerable conformational flexibility, as revealed by differing torsion angles in the atom sequence N-C-E-B-C ipso -C ortho . In the sulfur derivatives, the S-B bonds are all long (ca. 2.05Å), and the C-S bonds (ca. 1.73Å) are clearly lengthened compared to imidazole-2-thiones. The Se-B distance of 2.2111Å is the first selenone-borane bond length to be determined by X-ray analysis.

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“…[10] Dennoch beschrieben Denis et al die durch B(C 6 F 5 ) 3 katalysierte Dehydrokondensation beider Komponenten -H 3 P und BH 3 -bei hohen Temperaturen (90 8C), die zu einem Polymer der wahrscheinlichen Zusammensetzung [H 2 P-BH 2 ] n führt. [11] Es ist zweifelhaft, ob ein monomeres Phosphinoboran ein Intermediat einer solchen Reaktion ist (Schema 1). Andererseits existiert auch über Matrixisolationstechniken kein definierter Zugang zu Verbindungen der allgemeinen Formel H 2 E-E'H 2 (A).…”

Section: Professor Michael Veith Zum 65 Geburtstag Gewidmetunclassified

Kontrollierte Oligomerisierung von Lewis‐Säure/Base‐stabilisierten Phosphanylalanen

Bodensteiner

Vogel

Timoshkin³

et al. 2009

Angewandte Chemie

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Durch Feinabstimmung der Temperatur‐ und Lösungsmittelbedingungen gelingt die kontrollierte H2‐Eliminierung aus dem Lewis‐Säure/Base‐stabilisierten Phosphanylalan 1 (siehe Schema). Das entstehende cyclo‐Trimer 2 bildet durch weitere H2‐Eliminierung die Leiterverbindung 3. 2 und 3 sind die ersten Vertreter einer neuen Substanzklasse von 13/15‐Verbindungen ohne zusätzliche Donor‐Akzeptor‐Bindungen innerhalb des Gerüsts.

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B(C₆F₅)₃-catalyzed formation of B–P bonds by dehydrocoupling of phosphine–boranes

Abstract: Tris(pentafluorophenyl)borane was used as a new catalyst in the formation of P-B bonds by dehydrocoupling of phosphine-boranes.

Cited by 113 publications

References 11 publications

Lewis Base Stabilized Phosphanylborane

Lewis Base Stabilized Phosphanylborane

Sulfur and SeleniumActivation by Frustrated NHC/B(C₆F₅)₃ Lewis Pairs; Conformational Flexibility of Products

Kontrollierte Oligomerisierung von Lewis‐Säure/Base‐stabilisierten Phosphanylalanen

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B(C6F5)3-catalyzed formation of B–P bonds by dehydrocoupling of phosphine–boranes

Abstract: Tris(pentafluorophenyl)borane was used as a new catalyst in the formation of P-B bonds by dehydrocoupling of phosphine-boranes.

Cited by 113 publications

References 11 publications

Lewis Base Stabilized Phosphanylborane

Lewis Base Stabilized Phosphanylborane

Sulfur and SeleniumActivation by Frustrated NHC/B(C6F5)3 Lewis Pairs; Conformational Flexibility of Products

Kontrollierte Oligomerisierung von Lewis‐Säure/Base‐stabilisierten Phosphanylalanen

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B(C₆F₅)₃-catalyzed formation of B–P bonds by dehydrocoupling of phosphine–boranes

Sulfur and SeleniumActivation by Frustrated NHC/B(C₆F₅)₃ Lewis Pairs; Conformational Flexibility of Products