Recent topics of phosphine-mediated reactions

Karanam, Praneeth; Reddy, G. Madhusudhan; Koppolu, Srinivasa Rao; Lin, Wenwei

doi:10.1016/j.tetlet.2017.11.051

Cited by 47 publications

(18 citation statements)

References 70 publications

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“…Tertiary phosphines are unique and diverse Lewis bases that are widely used in many areas of synthetic chemistry. Applications range from their utilization as ubiquitous ligands in coordination or organometallic chemistry to phosphine‐catalyzed and stoichiometric phosphine‐mediated transformations. One of the main reasons for their broad range of applications is the intriguing ease with which the steric and electronic properties of phosphines can be rationally tuned using various substituents .…”

Section: Figurementioning

confidence: 99%

Pyridinylidenaminophosphines: Facile Access to Highly Electron‐Rich Phosphines

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Wilm

Werra

et al. 2019

Chemistry A European J

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Electron‐rich tertiary phosphines are valuable species in chemical synthesis. However, their broad application as ligands in catalysis and reagents in stoichiometric reactions is often limited by their costly synthesis. Herein, we report the synthesis and properties of a series of phosphines with 1‐alkylpyridin‐4‐ylidenamino and 1‐alkylpyridin‐2‐ylidenamino substituents that are accessible in a very short and scalable route starting from commercially available aminopyridines and chlorophosphines. The determination of the Tolman electronic parameter (TEP) value reveals that the electron donor ability can be tuned by the substituent pattern at the aminopyridine backbone and it can exceed that of common alkylphosphines and N‐heterocyclic carbenes. The potential of the new phosphines as strong nucleophiles in phosphine‐mediated transformations is demonstrated by the formation of Lewis base adducts with CO2 and CS2. In addition, the coordination chemistry of the new phosphines towards CuI, AuI, and PdII metal centers has been explored, and a convenient procedure to introduce the most basic phosphine into metal complexes starting from air‐stable phosphonium salt is described.

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Section: Figurementioning

confidence: 99%

Pyridinylidenaminophosphines: Facile Access to Highly Electron‐Rich Phosphines

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Wilm

Werra

et al. 2019

Chemistry A European J

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“…Chatani and co-workers furtherd eveloped an intramolecular quaternizationo faphosphino group with an aryl bromide to give six-membered phosphonium salt 45,w hich was transformed into 46 via CÀPc leavage (Scheme 16). [30] Them echanism of CÀPb ond activation is similar to that of the previously discussed reaction, butareducing reagent, (Me 3 Si) 3 SiH, was neededt oc overt palladium(II) into an activep alladium(0)s pecies.…”

Section: Phosphination With the Cleaved P-moietymentioning

confidence: 62%

“…[18] Althoughn ot fully optimizeda tt he time, the sider eactionw as developedi nto an efficient catalytic method for CÀPb ond transformation: one phenyl group from Ph 3 Pw as used as a benzo moiety to construct substituted naphthalene 25 with diphenylethyne through CÀHa nd CÀPb ond activations. The combination of an excessa mount of AgNO 3 [19] Cu(OAc) 2 was proposed as an oxidant to regenerate the active palladium(II) species. In competition studies with unsymmetrical tertiaryp hosphines, the phenylg roup is cleaved preferentially over the alkyl group, and the electron-deficient aryl group is more resistantt han that of the electron-rich substituent to CÀPb ondf ission, which indicates that the migrating aryl group in the reaction has nucleophilic character.D iphenylphosphinic acid( Ph 2 PO 2 H) was isolated as abyproduct after the reaction.…”

Section: Arylation With the Cleaved C-moietymentioning

confidence: 99%

“…Carbon–phosphorus (C−P) bond cleavage has attracted much research interest because of its significant role in modern organic synthesis, catalyst deactivation, and biological processes. For example, the industrially applicable Wittig reaction, and phosphine‐catalyzed or ‐mediated transformations of electron‐deficient unsaturated carbon–carbon bonds. Phosphonate degradation through C−P bond activation is quite common among ecosystems.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic Applications of Transition‐Metal‐Catalyzed C−P Bond Cleavage

Wang

Chen

Duan

2018

Chemistry An Asian Journal

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The wide occurrence of carbon-phosphorus bond activation in modern organic synthesis, catalyst deactivation, and biological process has attracted interest for synthetic applications. Over the past few decades, transition-metal-mediated transformations have become extremely powerful tools in organic synthesis. In this review, considerable progress that has been made in catalytic activations and transformations of carbon-phosphorus bonds within the coordination sphere of transition metals is described. Mechanistic information is also presented, and it is hoped that this review not only provides an account of the state of the art in the field, but also highlights the future potential of these reactions in organic synthesis.

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“…Many reviews have analyzed nucleophilic phosphine‐catalyzed reactions . In 2018, Lin and coworkers reviewed recent topics in phosphine‐mediated reactions . This review aimed to cover recent examples of these reactions not analyzed in nucleophilic phosphine‐catalyzed reactions with electron‐deficient allenes and alkynes and also highlight our contributions in unusual α‐addition reactions, which have been quite rare in traditional organophosphine chemistry.…”

Section: Introductionmentioning

confidence: 99%

Phosphine‐Catalyzed Reactions with Unsaturated Carbonyl Compounds

Nallapati

Chuang

2018

Asian J Org Chem

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Organophosphines are versatile Lewis basic catalysts that have been confirmed as powerful tools in organic synthesis for the past two decades. The nucleophilic addition of organophosphines to electron-deficient species can be divided into two categories: phosphine-catalyzed and stoichiometric phosphine-mediated transformations. In this focus review, we summarize recent examples of phosphine-catalyzed addition and annulation reactions with allenoates and alkynoates. In addition, we discuss our recent efforts in the development of unusual phosphine-mediated α-addition reactions with enynedioates, enynoates, and oligoynoates and its application in novel functional fullerene derivatives as n-type materials in organic photovoltaics.[a] Dr. Scheme 1. Phosphine-catalyzed Michael addition of arylcyanoacetates to allenoates. 2 3 4 5 6 7 8

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Recent topics of phosphine-mediated reactions

Cited by 47 publications

References 70 publications

Pyridinylidenaminophosphines: Facile Access to Highly Electron‐Rich Phosphines

Pyridinylidenaminophosphines: Facile Access to Highly Electron‐Rich Phosphines

Synthetic Applications of Transition‐Metal‐Catalyzed C−P Bond Cleavage

Phosphine‐Catalyzed Reactions with Unsaturated Carbonyl Compounds

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