Organometallic chemistry of bromodifluoromethyl substituted phosphines. The development of a novel nickel catalysed P–C bond forming reaction

Clarke, Matthew L.; Orpen, A. Guy; Pringle, Paul G.; Turley, Edward

doi:10.1039/b311799e

Cited by 24 publications

(12 citation statements)

References 14 publications

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“…However, coupling of Ph 2 PCF 2 Br with Ph 2 PSiMe 3 was catalyzed by the precursor Ni(dippf)Cl 2 , or related Ni(0) complexes (Scheme 51). A similar microwave-promoted coupling of CF 2 Br 2 with (i-Pr) 2 PSiCl 3 gave the bisphosphine directly, along with some monophosphine [83].…”

Section: Alkyl Halidesmentioning

confidence: 92%

Recent Advances in Metal-Catalyzed C–P Bond Formation

Glueck

2010

C-X Bond Formation

159

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This chapter describes recent advances in metal-catalyzed C-P bond formation, which may be classified into two types of reactions. In hydrophosphination and related processes, P-H groups add across unsaturated C-X (X ¼ C, N, O) bonds. Phosphination of electrophiles typically results in substitution at sp 2 or sp 3 carbon; the P-H group is removed, often by a base. The scope of both nucleophilic and electrophilic partners in these processes is surveyed, and the proposed mechanisms and intermediates in the metal-catalyzed reactions are described.

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Section: Alkyl Halidesmentioning

confidence: 92%

Recent Advances in Metal-Catalyzed C–P Bond Formation

Glueck

2010

C-X Bond Formation

159

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“…Notably, the title compound is quintessentially isostructural with: [PdCl 2 {P(C 6 H 11 ) 3 } 2 ] (Grushin et al, 1994); [PdBr 2 {P(C 6 H 11 ) 3 } 2 ] (Clarke et al, 2003); and [PdCl 2 {P(C 6 H 11 ) 2 (C 7 H 7 )} 2 ] (Vuoti et al, 2008) ((C 6 H 11 ) = cyclohexyl, (C 7 H 7 ) = o-tolyl). The Pd-P and Pd-X (X = Br and Cl) bond lengths were compared and it was observed that they were all within the same range of 2.3-2.4 Å.…”

Section: Methodsmentioning

confidence: 99%

trans-Dichloridobis[dicyclohexyl(phenyl)phosphane-κP]palladium(II)

2012

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The title compound, [PdCl2{P(C6H11)2(C6H5)}2], forms a monomeric complex with a trans-square-planar geometry. The Pd—P bond lengths are 2.3343 (5) Å, as the Pd atom lies on an inversion centre, while the Pd—Cl bond lengths are 2.3017 (4) Å. The observed structure was found to be closely related to [PdCl2{P(C6H11)3}2] [Grushin et al. (1994 ▶). Inorg. Chem. 33, 4804–4806], [PdBr2{P(C6H11)3}2] [Clarke et al. (2003 ▶). Dalton Trans. pp. 4393–4394] and [PdCl2P(C6H11)2(C7H7)}2] [Vuoti et al. (2008 ▶). Eur. J. Inorg. Chem. pp. 397–407] (C6H11 is cyclohexyl and C7H7 is o-tolyl). One of the cyclohexyl rings is disordered with the phenyl ring in a 0.587 (9):413 (9) ratio. Five long-range C—H⋯Cl interactions were observed within the structure.

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“…[PdBr 2 {P(C 6 H 11 ) 3 } 2 ] (Clarke et al, 2003); and [PdCl 2 {P(C 6 H 11 ) 2 (C 7 H 7 )} 2 ] (Vuoti et al, 2008) ((C 6 H 11 ) = cyclohexyl, (C 7 H 7 ) = o-tolyl). The Pd-P and Pd-X (X = Br and Cl) bond lengths were compared and it was observed that they were all within the same range of 2.3-2.4 Å.…”

Section: -Zmentioning

confidence: 99%

trans-Dichloridobis[dicyclohexyl(2,4,6-trimethylphenyl)phosphane-κP]palladium(II)

et al. 2012

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The title compound, [PdCl2(C21H33P)2], forms a monomeric complex with a trans-square-planar coordination geometry about the PdII atom which lies on an inversion centre. The Pd—P bond lengths are 2.3760 (13) Å, while the Pd—Cl bond lengths are 2.3172 (14) Å. The observed structure was found to be closely related to that of trans-dichloridobis[dicyclohexyl(phenyl)phosphane-κP]palladium(II), [PdCl2{P(C6H11)2(C6H5)}2] [Burgoyne et al. (2012 ▶). Acta Cryst. E68, m404].

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Organometallic chemistry of bromodifluoromethyl substituted phosphines. The development of a novel nickel catalysed P–C bond forming reaction

Abstract: A new nickel catalysed coupling reaction between phosphines of type Ph 2 PCF 2 Br and silyl-substituted phosphines is reported, along with the first example of a microwave assisted phosphine synthesis.

Cited by 24 publications

References 14 publications

Recent Advances in Metal-Catalyzed C–P Bond Formation

Recent Advances in Metal-Catalyzed C–P Bond Formation

trans-Dichloridobis[dicyclohexyl(phenyl)phosphane-κP]palladium(II)

trans-Dichloridobis[dicyclohexyl(2,4,6-trimethylphenyl)phosphane-κP]palladium(II)

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