The coordination chemistry of enantiopure diimines derived from 1-phosphanorbornadiene-2-carboxaldehydes

Germoni, Alexandre; Deschamps, Bernard; Ricard, Louis; Mercier, François; Mathey, François

doi:10.1016/j.jorganchem.2004.11.018

Cited by 14 publications

(5 citation statements)

References 18 publications

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“…The development of new and effective synthetic methods for polycyclic, rigid, bulky phosphorus(III) ligands, which might offer improved performance in homogeneous catalysis, is one of the current challenges in organophosphorus chemistry . Representative examples of polycyclic phosphines are NORBOS , BIPNOR , PennPhos , BABAR‐Phos , phosphanorbornadiene diimines , tricyclic phosphinites , or phenylphosphatrioxa‐adamantanes (Fig. ), which have been successfully used as ligands in asymmetric, biphasic, and homogeneous catalysis.…”

Section: Introductionmentioning

confidence: 99%

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

Zagidullin

Miluykov

Sinyashin

et al. 2013

Heteroatom Chemistry

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The [4+2] cycloaddition reaction of 1‐alkyl‐1,2‐diphospholes (1) with N‐phenylmaleimide proceeds at 25°С in toluene to give 1,7‐diphosphanorbornenes (2) as anti‐endo isomer only. Oxidation of 2 with air at room temperature or thionation with excess of sulfur at 80°С results in the formation of mixed valent PIII, PV 7‐oxo(thia)‐1,7‐diphosphanorbornenes (3, 4) in high yield. The polycyclic compounds 3 and 4 are air stable and have small sums of valence angles at the phosphorus atoms.

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Section: Introductionmentioning

confidence: 99%

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

Zagidullin

Miluykov

Sinyashin

et al. 2013

Heteroatom Chemistry

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“…60 Reaction with [Fe(Z 5 The reaction of an enantiopure formyl-substituted 1-phosphanorbornadiene with 1,2diaminocyclohexane results in the formation of 25. 61 The use of 25 as a tetradentate P 2 N 2 ligand was also described. An equilibrium between a five coordinate and a three coordinate phosphorus species, involving a hydrogen atom migration process has been described.…”

Section: Phosphorusmentioning

confidence: 99%

Nitrogen, phosphorus, arsenic, antimony and bismuth

Lynam

2006

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reviews the literature reported during 2005 on the chemistry of nitrogen, phosphorus, arsenic, antimony and bismuth. PreambleOnce again the study of the chemistry of the pnictogens has provided considerable challenges to both synthetic and theoretical chemists. Significant new advances and insights into have been made, of particular note are the developments in the areas of activation of dinitrogen, such as the work of Schrock on molybdenum complexes 1,2 and the discovery of an amido-hydride complex from activation of ammonia. 3 Further highlights include the continued expansion of the use of metal phosphinidene complexes as synthetic reagents for the production of novel phosphoruscontaining materials and the synthesis of several new cationic arsenic-containing species.As in previous years and due to space restrictions this review will not, in general, consider the use of the trivalent elements as ligands, however reviews on ''user friendly'' primary phosphines 4 and how to evaluate the net donor abilities of phosphines 5 have appeared. NitrogenThe activation of dinitrogen remains a major area of interest. The molybdenumcentred reduction of dinitrogen to ammonia remains one of the most impressive methods of nitrogen fixation and a review on this subject has appeared 1 as has a comprehensive study into several aspects of this chemistry. 2 It has been shown that under an atmosphere of N 2 , the dimer [Ta(Z 5 -C 5 Me 4 R)] 2 (m-Cl) 4 (R = Me, Et) disproportionates to give [Ta(Z 5 -C 5 Me 4 R)] 2 (m-Z 1 ,Z 1 -N 2 ) as the nitrogen-containing product. 6 The dinitrogen may be considered to have undergone a four-electron reduction with the tantalum now existing in the (V) oxidation state. In a similar fashion, reduction of [Ti(Z 5 -C 5 Me 5 )Cl 3 ] in the presence of substituted fulvene gives rise to dinuclear species containing a (m-Z 1 , Z 1 -N 2 ) ligand. 7 The reduction of the zirconium complex [NPN]ZrCl 2 (thf) [NPN = PhP(CH 2 SiMe 2 NPh) 2 ] under nitrogen results in the formation of [NPN]Zr(m-Z 2 , Z 2 -N 2 )(thf). 8 A similar reaction with the titanium analogue results in the insertion of dinitrogen into the Ti-PPh bond and formation of 1. Using a related ligand set within the coordination sphere of tantalum, Fryzuk has also shown that it is possible to convert hydrazine to bridging Ta-NH-Ta groups. 9 A reaction of the same precursor with Me 2 NNH 2 results in the formation of a complex containing a bridging nitride ligand. The oxidative addition

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“…1) with the phosphorus atom embedded in a five-or six-membered ring were shown to be highly efficient chiral ligands (BIPNOR A [5], PennPhos B [6], 9-PBN C [7] Briphos D [8], phosphabarrelene E [9], tricyclic phosphinite F [10], 1-phosphanorbornadiene-oxazoline G [11]) and excellent chiral organocatalysts (2-aza-5-phosphabicyclo[2.2.1]heptane H [12], 7-phosphabicyclo-[2.2.1]heptane I [13]). The main structural feature of these chiral phosphines is their rigid framework and a chiral, not racemizable P-atom situated at the bridgehead of a bicyclic system [14], which excludes the conformational flexibility associated with other cyclic chiral phosphines and provides a new motif for chiral phosphine design. However, the preparation of these phosphines is rather complicated and mostly based on expensive starting materials or complex separation of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Сhiral tricyclic phosphines derived from 1-(+)-neomenthyl-1,2-diphosphole: Synthesis and applications in asymmetric homogeneous catalysis

et al. 2017

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The coordination chemistry of enantiopure diimines derived from 1-phosphanorbornadiene-2-carboxaldehydes

Cited by 14 publications

References 18 publications

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

Nitrogen, phosphorus, arsenic, antimony and bismuth

Сhiral tricyclic phosphines derived from 1-(+)-neomenthyl-1,2-diphosphole: Synthesis and applications in asymmetric homogeneous catalysis

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