Copper(I)-catalyzed hydrophosphination of styrenes

Leyva‐Pérez, Antonio; Vidal‐Moya, Alejandro; Cabrero‐Antonino, Jose R.; Al-Deyab, Salem S.; Al‐Resayes, Saud I.; Corma, Avelino

doi:10.1016/j.jorganchem.2010.09.069

Cited by 51 publications

(36 citation statements)

References 38 publications

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“…Originally, this type of catalysis was very dependent on rhodium, palladium, and platinum. More recently, a limited variety of competent precatalysts based on copper,51 iron,50f tin,52 or more oxophilic metals, e.g., titanium/zirconium,53 alkaline earths,16 and divalent lanthanides have also been revealed 16b,16d,54. Like others, we have been interested in exploiting oxophilic Ae complexes to create CP σ‐bonds, since such compounds designed around hard elements, less prone to interacting with phosphines (i.e., to be deactivated upon excessively strong coordination of this substrate) than late‐transition complexes, could offer significant advantages over these other types of more traditional precatalysts.…”

Section: Hydrophosphination Catalysismentioning

confidence: 99%

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Sarazin

Carpentier

2016

The Chemical Record

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The large alkaline earths (Ae), calcium, strontium and barium, have in the past 15 years yielded a brand new generation of heteroleptic molecular catalysts for the production of fine chemicals. However, the integrity of these complexes is often plagued by ligand redistribution equilibria in solution. This personal account retraces the paths followed in our research group towards the design of stable heteroleptic alkalino-earth complexes, including the use of intramolecular noncovalent Ae···H-Si and Ae···F-C interactions. Their implementation as homogenous precatalysts for reactions such as the intramolecular and intermolecular hydroamination and hydrophosphination of activated alkenes, the hydrophosphonylation of ketones, and the dehydrogenative coupling of amines and hydrosilanes that enable the efficient and controlled formations of CP, CN, or SiN σ-bonds, is presented in a synthetic perspective that highlights their overall outstanding catalytic performance.

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Section: Hydrophosphination Catalysismentioning

confidence: 99%

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Sarazin

Carpentier

2016

The Chemical Record

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“…[57] Although FeCl 3 and Fe(NTf 2 ) 3 gave linear, b-addition products 83 in low to moderate yields, Fe(OTf) 3 catalysed the reaction in good yields and gave hydrophosphination products 83 and 84 in a 3:1 ratio. On the basis of the substrate scope reported by Taillefer and Gaumont, [54] the inefficiency of the iron(III)-cata- lysed reactions reported by Corma might be attributed to reaction optimisation with a styrene derivative bearing an electron-withdrawing group.…”

Section: Hydrophosphination Of Alkenes and Alkynesmentioning

confidence: 98%

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

2014

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The metal‐catalysed hydrofunctionalisation of alkenes and alkynes provides a convenient and atom‐economic route to diversely functionalised products with control of regio‐, chemo‐ and stereoselectivity. As one of the most abundant elements on earth, iron offers a level of sustainable and long‐term availability that is uncommon for most transition metals. Although iron is commonly found in the oxidation states of +2 and +3, the use of redox‐active ligands has allowed the synthesis and application of low oxidation state iron complexes in catalysis. A broad range of hydrofunctionalisation reactions have been developed by using iron catalysts in a wide variety of oxidation states. Intense development over the past decade has resulted in the development of iron‐catalysed hydroamination, hydroalkoxylation, hydrocarboxylation, hydrothiolation, hydrovinylation, hydrosilylation, hydroboration, hydrophosphination, hydromagnesiation and carbonylation reactions, amongst others. With the field still in its infancy, there is great potential for further developments in the mechanistic understanding and synthetic and industrial applicability of these processes.

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“…[119] There are various important processes reported for the hydrophosphanation of alkenes catalyzed by Pd and Ni complexes. [121] Alonso et al [4g] investigated the hydrophosphanation of alkenes in the absence of a catalyst, with no solvent, and in re-gioselectively. Other reported protocols also suffered drawbacks, such as expensive and toxic and harsh reactions conditions.…”

Section: Conventional Heating and Room Temperaturementioning

confidence: 99%

“…Other reported protocols also suffered drawbacks, such as expensive and toxic and harsh reactions conditions. [121] Alonso et al [4g] investigated the hydrophosphanation of alkenes in the absence of a catalyst, with no solvent, and in re-gioselectively. First, the effect of solvent was investigated for the model reaction between diphenylphosphine and styrene at 70 8C under an Ar atmosphere (to prevent the in situ oxidation of diphenylphosphine to the resultant phosphine oxide).…”

Section: Conventional Heating and Room Temperaturementioning

confidence: 99%

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

Gawande¹,

Bonifácio²,

Luque³

et al. 2013

ChemSusChem

271

122

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In the past decade, alternative benign organic methodologies have become an imperative part of organic syntheses and chemical reactions. The various new and innovative sustainable organic reactions and methodologies using no solvents or catalysts and employing alternative energy inputs such as microwaves, sonication, conventional and room temperature heating conditions, mechanochemical mixing, and high-speed ball milling are discussed in detail. Environmentally benign and pharmaceutically important reactions such as multicomponent, condensation, and Michael addition reactions; ring opening of epoxides; and oxidation and other significant organic reactions are discussed. An overview of benign reactions through solvent- and catalyst-free (SF-CF) chemistry and a critical perspective on emerging synergies between SF-CF organic reactions are discussed.

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Copper(I)-catalyzed hydrophosphination of styrenes

Cited by 51 publications

References 38 publications

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

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