scholarly journals Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

2020 ◽  
Author(s):  
Megan Greaves ◽  
Thomas O. Ronson ◽  
Guy Lloyd-Jones ◽  
Feliu Maseras ◽  
Stephen Sproules ◽  
...  
Keyword(s):  
Alkyl Radical ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Active Species ◽  
Alkyl Halides ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Alternative Pathways ◽  
Cross Coupling Reactions ◽  
Abstraction Reaction

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(dppf)2], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The yields in prototypical nickel-catalysed Kumada cross-coupling reactions are shown to be improved by the addition of free phosphine ligands<br>

scholarly journals Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

2020 ◽  
Author(s):  
Megan Greaves ◽  
Thomas O. Ronson ◽  
Guy Lloyd-Jones ◽  
Feliu Maseras ◽  
Stephen Sproules ◽  
...  
Keyword(s):  
Alkyl Radical ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Active Species ◽  
Alkyl Halides ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Alternative Pathways ◽  
Cross Coupling Reactions ◽  
Abstraction Reaction

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(dppf)2], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The yields in prototypical nickel-catalysed Kumada cross-coupling reactions are shown to be improved by the addition of free phosphine ligands<br>

Ni(COD)(DMFU): A Heteroleptic 16-Electron Precatalyst for 1,2-Diarylation of Alkenes

Synlett ◽  
2021 ◽  
Author(s):  
Nana Kim ◽  
Van T. Tran ◽  
Omar Apolinar ◽  
Steven Wisniewski ◽  
Martin Eastgate ◽  
...  
Keyword(s):  
Nickel Complex ◽  
Active Catalyst ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Beneficial Effects ◽  
Cross Coupling Reactions ◽  
Growing Body ◽  
Hydride Elimination

Electron-deficient olefin (EDO) ligands are known to promote a variety of nickel-catalyzed cross-coupling reactions, presumably by accelerating the reductive elimination step and preventing undesired β-hydride elimination. While there is a growing body of experimental and computational evidence elucidating the beneficial effects of EDO ligands, significant gaps remain in our understanding of the underlying coordination chemistry of the Ni–EDO species involved. In particular, most procedures rely on in situ assembly of the active catalyst, and there is a paucity of pre-ligated Ni-EDO precatalysts. Herein, we investigate the 16-electron, heteroleptic nickel complex, Ni(COD)(DMFU), and examine the performance of this complex as a precatalyst in 1,2-diarylation of alkenes.

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

2020 ◽  
Vol 2020 (9) ◽  
pp. 1122-1128
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

scholarly journals Perfluorinated phosphine and hybrid P–O ligands for Pd catalysed C–C bond forming reactions in solution and on Teflon supports

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

Phosphine ligands containing a perfluorous ponytail can be sorbed onto Teflon tape and used as ligands for C–C cross coupling reactions with little leaching.

scholarly journals Synthesis, Structural Analysis and Application of Aryl‐Diadamantyl Phosphine ligands in Palladium Catalyzed Cross‐Coupling Reactions

2020 ◽  
Vol 2020 (34) ◽  
pp. 5634-5634
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Air-stable Pd(0) catalyst bearing dual phosphine ligands: a detailed evaluation of air stability and catalytic property in cross-coupling reactions

2020 ◽  
Vol 49 (36) ◽  
pp. 12814-12819
Author(s):  
Ryota Sato ◽  
Takaki Kanbara ◽  
Junpei Kuwabara
Keyword(s):  
Catalytic Activity ◽  
Catalytic Property ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Donor And Acceptor ◽  
Detailed Evaluation ◽  
Good Catalytic Activity

The Pd(0) complex bearing donor and acceptor phosphine ligands shows long-term air stability and good catalytic activity even in a reaction with a relatively inactive substrate.

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