Exploring the Catalytic Reactivity of Nickel Phosphine–Phosphite Complexes

2015 ◽  
Vol 68 (12) ◽  
pp. 1842 ◽  
Author(s):  
Sven S. Kampmann ◽  
Nikki Y. T. Man ◽  
Allan J. McKinley ◽  
George A. Koutsantonis ◽  
Scott G. Stewart
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Phosphine Complexes ◽  
Cross Coupling Reactions ◽  
Catalytic Reactivity ◽  
Nickel Phosphine

In this study, we present an investigation into various nickel phosphite and phosphite–phosphine complexes for use in the Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions and the ammonia arylation reaction. In these coupling reactions, it was discovered that the Ni[P(OEt)3]4, (dppf)Ni[P(OPh)3]2, and (binap)Ni[P(OPh)3]2 catalysts were the most effective. In addition, an optimisation process for these catalytic systems as well as functional group compatibility are discussed.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

scholarly journals Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis

2015 ◽  
Vol 112 (39) ◽  
pp. 12026-12029 ◽  
Author(s):  
Yohei Yamashita ◽  
John C. Tellis ◽  
Gary A. Molander
Keyword(s):  
Small Molecules ◽  
Functional Group ◽  
Cross Coupling ◽  
Differential Protection ◽  
Coupling Reactions ◽  
Protecting Group ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Rapid Construction ◽  
Metal Catalyzed

Orthogonal reactivity modes offer substantial opportunities for rapid construction of complex small molecules. However, most strategies for imparting orthogonality to cross-coupling reactions rely on differential protection of reactive sites, greatly reducing both atom and step economies. Reported here is a strategy for orthogonal cross-coupling wherein a mechanistically distinct activation mode for transmetalation of sp3-hybridized organoboron reagents enables C-C bond formation in the presence of various protected and unprotected sp2-hybridized organoborons. This manifold has the potential for broad application, because orthogonality is inherent to the activation mode itself. The diversification potential of this platform is shown in the rapid elaboration of a trifunctional lynchpin through various transition metal-catalyzed processes without nonproductive deprotection or functional group manipulation steps.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

Structural features and catalytic reactivity of [Pd{(Ph2P)2N(CH2)3Si(OCH3)3-κP,P′}I2] and related complexes in hydroalkoxycarbonylation and Suzuki–Miyaura C−C cross-coupling reactions

Polyhedron ◽  
2018 ◽  
Vol 151 ◽  
pp. 292-298 ◽  
Author(s):  
Ioannis K. Stamatopoulos ◽  
Maria Kapsi ◽  
Maria Roulia ◽  
Georgios C. Vougioukalakis ◽  
Catherine P. Raptopoulou ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Structural Features ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Catalytic Reactivity

scholarly journals Well-Defined Pre-Catalysts in Amide and Ester Bond Activation

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 215 ◽  
Author(s):  
Sandeep R. Vemula ◽  
Michael R. Chhoun ◽  
Gregory R. Cook
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Ester Bond ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Design And Synthesis ◽  
Cross Coupling Reactions ◽  
Made In

Over the past few decades, transition metal catalysis has witnessed a rapid and extensive development. The discovery and development of cross-coupling reactions is considered to be one of the most important advancements in the field of organic synthesis. The design and synthesis of well-defined and bench-stable transition metal pre-catalysts provide a significant improvement over the current catalytic systems in cross-coupling reactions, avoiding excess use of expensive ligands and harsh conditions for the synthesis of pharmaceuticals, agrochemicals and materials. Among various well-defined pre-catalysts, the use of Pd(II)-NHC, particularly, provided new avenues to expand the scope of cross-coupling reactions incorporating unreactive electrophiles, such as amides and esters. The strong σ-donation and tunable steric bulk of NHC ligands in Pd-NHC complexes facilitate oxidative addition and reductive elimination steps enabling the cross-coupling of broad range of amides and esters using facile conditions contrary to the arduous conditions employed under traditional catalytic conditions. Owing to the favorable catalytic activity of Pd-NHC catalysts, a tremendous progress was made in their utilization for cross-coupling reactions via selective acyl C–X (X=N, O) bond cleavage. This review highlights the recent advances made in the utilization of well-defined pre-catalysts for C–C and C–N bond forming reactions via selective amide and ester bond cleavage.

Directed ortho Metalation (DoM)-Linked Corriu–Kumada, Negishi, and Suzuki–Miyaura Cross-Coupling Protocols: A Comparative Study

Synthesis ◽  
2018 ◽  
Vol 50 (22) ◽  
pp. 4395-4412 ◽  
Author(s):  
Victor Snieckus ◽  
Claude Quesnelle
Keyword(s):  
Transition Metal ◽  
Comparative Study ◽  
Systematic Study ◽  
Functional Group ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Ortho Metalation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (DoM) is reported. In general, the Suzuki–Miyaura and Negishi protocols show greater scope and better yields than the Corriu–Kumada variant, although the latter qualitatively proceeds at fastest rate but has low functional group tolerance. The Negishi process is shown to be useful for substrates with nucleophile and base-sensitive functionality and it is comparable to the Suzuki–Miyaura reaction in efficiency. The link of these cross-coupling reactions to the DoM strategy lends itself to the regioselective construction of diversely substituted aromatics and heteroaromatics.

P2Et Phosphazene: A Mild, Functional Group Tolerant Base for Soluble, Room Temperature Pd-Catalyzed C–N, C–O, and C–C Cross-Coupling Reactions

2015 ◽  
Vol 17 (13) ◽  
pp. 3370-3373 ◽  
Author(s):  
Alexander Buitrago Santanilla ◽  
Melodie Christensen ◽  
Louis-Charles Campeau ◽  
Ian W. Davies ◽  
Spencer D. Dreher
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions

2020 ◽  
Vol 17 (5) ◽  
pp. 589-604
Author(s):  
Jaishri Chopra ◽  
Ajay K. Goswami ◽  
Prabhat K. Baroliya
Keyword(s):  
Large Scale ◽  
Supported Catalysts ◽  
Supported Catalyst ◽  
Cross Coupling ◽  
Nickel Catalysts ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Heterogeneous Catalytic ◽  
Cross Coupling Reactions ◽  
Simple Filtration

Solid supported catalysts have been of considerable interest in organic synthesis for the last few years. Solid support provides an efficient heterogeneous catalytic system owing to facile recovery and extensive recycling by simple filtration because of possessing 3-R approach (Recoverable, Robust and Recyclable) and makes solid supported catalyst more appealing nowadays. In view of the high cost and shortage of furthermost used palladium catalyst, its recovery and recycling are vital issues for any large-scale application which are being overcome by using solid supported catalytic systems. Therefore, a variety of inorganic and organic solid-supported catalytic systems have been developed so far in order to address these challenges. This review attempts highlight a number of solid supported catalytic systems in the pro-active area of widely used C-C cross coupling reactions.

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