Synthesis and structure of new chiral ferrocenylphosphines for asymmetric catalysis

Togni, Antonio; Breutel, Claude; Soares, Marie C.; Zanetti, Nadia C.; Gerfin, Tobias; Gramlich, Völker; Spindler, Felix; Rihs, Grety

doi:10.1016/0020-1693(94)03912-7

Cited by 66 publications

(29 citation statements)

References 33 publications

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“…Similar ring-inversion processes have been observed previously for six-membered chelate rings in ferrocenyldiphosphane transition metal complexes. [3,15,16] The spectrum recorded at 80°C is in line with the trend observed at lower temperature. Only one tightly coupled ABM system is found which accounts for the fast interconversion of the two conformers.…”

Section: P{ 1 H} Vt Nmr Study Of Complex 1bsupporting

confidence: 84%

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Complexes of Rhodium(I) and Iridium(I) with the Chiral Tridentate Phosphane Pigiphos: Structure and Reactivity Studies

Hintermann

Perseghini

Barbaro³

et al. 2003

Eur J Inorg Chem

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The chiral ferrocenyltriphosphane Pigiphos [bis{(S)‐1‐[(R)‐2‐(diphenylphosphanyl)ferrocenyl]ethyl}cyclohexylphosphane] forms four‐coordinate complexes with IrI and RhI. The tridentate ligand assumes different conformations in the derivatives [Rh(CO)(Pigiphos)]OTf (4) and [IrCl(Pigiphos)] (1b), the latter also showing a drastic deviation from the square‐planar geometry. Reactivity studies have focussed on the more reactive 1b. The HCl and O2 adducts have been characterized in solution. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: P{ 1 H} Vt Nmr Study Of Complex 1bsupporting

confidence: 84%

“…It is worth noting that in most of the Josiphos-type ferrocenyldiphosphane complexes the six-membered chelate ring adopts a distorted boat conformation. [3,15,16] …”

Section: Solid-state Structure Ofmentioning

confidence: 99%

Complexes of Rhodium(I) and Iridium(I) with the Chiral Tridentate Phosphane Pigiphos: Structure and Reactivity Studies

Hintermann

Perseghini

Barbaro³

et al. 2003

Eur J Inorg Chem

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“…As a result of the difficulties associated with the reduction of the phosphine oxides, we sought an alternative route to the optically pure phosphines 10a and b. We noted that they were separable (with difficulty) by chromatography and so we adapted the general Merck procedure of coupling secondary phosphines to aryl triflates [11] by reacting (R)-methoxy triflate 4 with racemic anisylphenylphosphine [12] Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

P-chirogenic phosphines. MOP/diPAMP hybrids, their oxide crystal structures, reduction studies and alternative syntheses

Higham

Clarke

Müller‐Bunz

et al. 2005

Journal of Organometallic Chemistry

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“…Amination of aryl bromides and chlorides: Hartwig first reported the high yielding amination of unactivated aryl chlorides under mild conditions by using D t BPF bis(di-tert-butylphosphino)ferrocene [138,139] and similar sterically hindered bis(phosphine) ligands developed by Spindler, Togni, and Bläser for asymmetric hydrogenations [140][141][142]. Activated aryl chlorides react much like unactivated aryl bromides, and reactions of these substrates with the original catalyst based on tri-ortho-tolyl phosphine were reported [143].…”

Section: Use Of Sterically Hindered Bis(phosphine) Ligandsmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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Synthesis and structure of new chiral ferrocenylphosphines for asymmetric catalysis

Cited by 66 publications

References 33 publications

Complexes of Rhodium(I) and Iridium(I) with the Chiral Tridentate Phosphane Pigiphos: Structure and Reactivity Studies

Complexes of Rhodium(I) and Iridium(I) with the Chiral Tridentate Phosphane Pigiphos: Structure and Reactivity Studies

P-chirogenic phosphines. MOP/diPAMP hybrids, their oxide crystal structures, reduction studies and alternative syntheses

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

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