1,1′,2,2′-Tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene, a new cisoid arrangement of phosphino groups

Broussier, R.; Bentabet, Emmanuelle; Amardeil, Régine; Richard, Philippe; Meunier, Philippe; Kalck, Philippe; Gautheron, B.

doi:10.1016/s0022-328x(01)00883-x

Cited by 17 publications

(27 citation statements)

References 34 publications

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“…Table 2 displays salient results obtained with dppf, 3, for the amination of allylacetate with aniline (entries [12][13][14][15][16][17][18][19][20]. These experiments have been conducted to check the performances and the limitations of dppf as auxiliary ligand in allylic substitution.…”

Section: Pd-11 -Bis(diphenylphosphino)ferrocene System In Amination mentioning

confidence: 99%

“…The reaction rate decreases in the absence of solvent (yield 98% in 6 h, selectivity 91%, entry 13) or in water (yield 84% in 60 h, selectivity 79%, entry 14); this is presumably due to mass transfer limitations. The substrate to catalyst ratio can be substantially increased (entries [15][16][17][18][19][20]. At ratio S : C = 500, 1000, 5000, 10 000 and even 100 000, high conversions are reached in 2-70 h. Complete conversions with yields of expected product above 90% are obtained at 500 ≤ S : C ≤ 10 000 (entries 15-18).…”

Section: Pd-11 -Bis(diphenylphosphino)ferrocene System In Amination mentioning

confidence: 99%

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Efficient palladium–ferrocenylphosphine catalytic systems for allylic amination of monoterpene derivatives

Nguyên¹,

Urrutigoı̈ty²,

Fihri³

et al. 2006

Applied Organom Chemis

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Ferrocenylphosphines added to [Pd(µ-Cl)(η 3 -C 3 H 5 )] 2 dimeric precursor produce efficient catalysts to effect the allylic amination of terpenic allylacetates. Particularly convenient are tetrakis(diphenylphosphino)ferrocene and 1,1 -bis(diphenylphosphino)ferrocene, which allow the amination of allylacetates with good to excellent selectivity, and have turnover numbers as high as 80 000, for instance, for the formation of allylaniline. Herein, we report on reactions that selectively transform geranylacetate, nerylacetate, linalylacetate and perillylacetate into the corresponding allylic amines. These preparative methods give facile access to various products of great potential industrial interest.

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Section: Pd-11 -Bis(diphenylphosphino)ferrocene System In Amination mentioning

confidence: 99%

Section: Pd-11 -Bis(diphenylphosphino)ferrocene System In Amination mentioning

confidence: 99%

Efficient palladium–ferrocenylphosphine catalytic systems for allylic amination of monoterpene derivatives

Nguyên¹,

Urrutigoı̈ty²,

Fihri³

et al. 2006

Applied Organom Chemis

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“…1. In addition Broussier et al [5] have reported the elegant synthesese of poly-phosphinoferrocenes using appropriately substituted cyclopentadienes as ferrocene precursors.As previously noted, there are two possible synthetic routes to the tri-substituted compounds the first using 1,2,3-tris (dimethylaminomethyl)ferrocene 3 as precursor to compound tris-phosphine 8 by following the methodology adopted, [3] for the bis-methylamine compound, although initial results were unpromising. It was originally thought that Eschenmoser's salt was insufficiently electrophilic to substitute the 3-position of the largely deactivated disubstituted ferrocene.…”

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confidence: 99%

“…1. In addition Broussier et al [5] have reported the elegant synthesese of poly-phosphinoferrocenes using appropriately substituted cyclopentadienes as ferrocene precursors.…”

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The first 1,2,3-tris(phosphinomethyl)ferrocene

Butler

Fortune

Morris

et al. 2004

Inorganic Chemistry Communications

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“…Conversely, in the favored conformation found for 18 ( Figure 1, right) the four phosphorus atoms point towards the same half-space as a result of steric factors attributed to the hindering tert-butyl groups; the phenyl groups are also interlocked (P2 and P3 are in the eclipsed conformation). [35] In solution, NMR spectroscopic experiments indicated that the conformation of 18 is restricted, similarly to the solid state, exhibiting an AAЈBBЈ spin-system pattern. The cisoid conformation for the tert-butylated tetraphosphane was conserved in solution above 90°C, as attested by 31 P NMR spectroscopy in [D 8 ]toluene.…”

Section: Performances Of Ferrocenylphosphanes In Heck and Suzuki Reacmentioning

confidence: 99%

Ultra‐Low Catalyst Loading as a Concept in Economical and Sustainable Modern Chemistry: The Contribution of Ferrocenylpolyphosphane Ligands

2007

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The challenge of sustainability in modern chemistry will be met with new technologies and processes provided significant progress is made in several key research areas, such as the expansion of chemistry from renewable feedstock, the design of environmentally benign chemicals and solvents, the minimization of depletive resources, and the development of high‐performance catalysis. In this prospect, ligand chemistry is a pivotal science that links modern‐organic,‐inorganic, ‐organometallic, and ‐coordination chemistry through a vast number of valuable applications, precisely associated to catalysis. We review in this article our recent work on catalysis promoted by original ferrocenyl tetra‐, tri‐, and diphosphane ligands. New concepts, taking advantages of this family of branched multidentate ligands, have led to progress in homogeneous catalysis. The search for catalyst longevity and ultra‐low catalyst loadings (high turnover numbers), on the basis of multidentarity effects and robustness of the ferrocenyl backbone were focused on high‐value palladium‐catalyzed C–C cross‐couplings, such as Heck, Suzuki, and Sonogashira reactions. Low catalyst loading was also explored for C–N cross‐coupling in the allylic amination of achiral substrates. The advantages of this newly born family of ligands in the class of multidentate compounds are discussed in light of the valuable information gathered up to now on their reactivity, structure, and mechanistic behavior.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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1,1′,2,2′-Tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene, a new cisoid arrangement of phosphino groups

Cited by 17 publications

References 34 publications

Efficient palladium–ferrocenylphosphine catalytic systems for allylic amination of monoterpene derivatives

Efficient palladium–ferrocenylphosphine catalytic systems for allylic amination of monoterpene derivatives

The first 1,2,3-tris(phosphinomethyl)ferrocene

Ultra‐Low Catalyst Loading as a Concept in Economical and Sustainable Modern Chemistry: The Contribution of Ferrocenylpolyphosphane Ligands

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