New mono- and bidentate P-ligands using one-pot click-chemistry: synthesis and application in Rh-catalyzed hydroformylation

Dubrovina, Natalia V.; Domke, Lutz; Shuklov, Ivan A.; Spannenberg, Anke; Franke, Robert; Villinger, Alexander; Börner, Armin

doi:10.1016/j.tet.2013.07.070

Cited by 32 publications

(13 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…182 mg (96%) of beige solid was obtained; mp: 77–79 °C (lit. 40 77–78 °C); 1 H NMR (400 MHz; DMSO-d 6 ; TMS): δ 8.01 (s, 1H, CH), 7.28–7.40 (m, 5H, Ar), 5.57 (s, 2H, ArCH 2 N), 5.16 (t, J = 5.7 Hz, 1H, OH), 4.51 (d, J = 5.5 Hz, 2H, CH 2 OH); 13 C NMR (101 MHz; DMSO-d 6 ; TMS): δ 148.8, 136.6, 129.2, 128.6, 128.4, 123.3, 55.6, 53.2.…”

Section: Methodsmentioning

confidence: 99%

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Mularski

Czaplińska

Cieślik

et al. 2018

Sci Rep

View full text Add to dashboard Cite

Electrolytic copper is a well-known form of pure, oxygen free copper that is used for industrial applications. In this work, the catalytic potential of this relatively cheap material was studied. The addition of less than 0.015 mol equivalent of copper powder effectively catalysed the one-pot synthesis of triazoles from a diverse range of organic halides and alkynes. Quantitative conversions in aqueous solvents can be achieved within minutes. The heterogenous nature of the catalyst afforded a low level of copper contamination in the products, thus meeting the rigorous criteria of the pharmaceutical industry.

show abstract

Section: Methodsmentioning

confidence: 99%

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Mularski

Czaplińska

Cieślik

et al. 2018

Sci Rep

View full text Add to dashboard Cite

show abstract

“…Application References pyridyl phosphines OLEDs [13] Heck coupling [14] metal organic frameworks [15] polymerization of lactides [16] alkene hydroxylation [17] addition reaction [18] ethylene oligomerization [19] synthesis of pyrazolines [20] triazolyl phosphines Suzuki cross coupling [21] asymmetric hydrogenation [22] luminescence [23] hydroformylation [24] pyrazolyl phosphines coordination polymers [25] Heck coupling [26] imidazolyl phosphines Suzuki coupling [27] hydroamination [28] OLEDs [29] ethylene oligomerization [30] amination [31] olefin metathesis [32] hydroformylation [33] pyrrolyl phosphines hydroformylation [34,35] ethylene polymerization [36] oxazolyl phosphines asymmetric cycloaddition [37] asymmetric hydrogenation [38] carbonylation of alkynes [39] allylic substitution [40] asymmetric addition [41] allylic amination [42,43] The presence of soft donor atoms such as phosphorus results in the formation of hemilabile ligands. These are multidentate ligands having hard P-donor and soft N-and/or O-donor atoms [44].…”

Section: Type Of Ligandmentioning

confidence: 99%

Architecture and synthesis of P,N-heterocyclic phosphine ligands

Munzeiwa¹,

Omondi²,

Nyamori³

2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N-heterocycles. This discussion seeks to paint a broad picture and consolidate different synthetic protocols and techniques for N-heterocyclic phosphine motifs. The introduction provides an account of P,N-phosphine ligands, and their structural and coordination benefits from combining heteroatoms with different basicity in one ligand. The body discusses the synthetic protocols which focus on P–C, P–N-bond formation, substrate and nucleophile types and different N-heterocycle construction strategies. Selected references are given in relation to the applications of the ligands.

show abstract

“…53 Currently Routes A and B are the most useful tools for the construction of 5-iodotriazoles due to the simplicity of the procedures, accessibility of the starting materials, and their tolerance to various functional groups. However diazotization (Route D), [54][55][56] lithiation followed by metal-iodine exchange (Route E), [57][58][59][60][61] and direct iodination of triazoles (Route E) 62 are also utilized.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

Danilkina

Govdi²,

Балова³

2020

Synthesis

View full text Add to dashboard Cite

Copper-catalyzed azide–alkyne cycloaddition is a useful tool for the synthesis of both 1,2,3-triazoles and 5-iodo-1H-1,2,3-triazoles starting from either terminal alkynes or iodoalkynes. 5-Iodotriazoles have been recognized as very useful building blocks for the synthesis of diverse 1,4,5-trisubstituted 1,2,3-triazoles. Synthetic application of 5-iodo-1,2,3-triazoles through the creation of a new C–C, C–heteroatom, or C–D(T) bond along with the application areas of both iodotriazoles and products of their modification including radiolabeled compounds are discussed.1 Introduction2 Synthetic Approaches to 5-Iodo-1H-1,2,3-triazoles3 5-Iodotriazoles in C–C Bond Formation3.1 Intermolecular C–C Cross-Coupling3.2 Intramolecular Cross-Coupling: Direct Arylation and C–I/C–I Homocoupling3.3 Other Transformations4 5-Iodotriazoles in Radiolabeling, Halogen Exchange, and Heterocoupling Reactions5 Summary

show abstract

New mono- and bidentate P-ligands using one-pot click-chemistry: synthesis and application in Rh-catalyzed hydroformylation

Cited by 32 publications

References 32 publications

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Architecture and synthesis of P,N-heterocyclic phosphine ligands

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

Contact Info

Product

Resources

About