chemia: Negishi coupling

Evidence: 47 • authority: 80

Heterogeneous Bifunctional Ni Single-Atom Catalyst on Carbon Nitride for Selective C(sp2)C(sp3) Coupling

Evidence: 47 • authority: 80

Heterogeneous Metallaphotocatalytic C(sp2)C(sp3) Cross-Coupling Reactions with Integrated Bipyridyl-Ni(II)-Carbon Nitride

Evidence: 47 • authority: 72

The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon–carbon bonds (C–C) in the process. A palladium (0) species is generally utilized as the catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc. R − X + R ′ − Zn X ′ → PdL n or NiL n R − R ′ {\displaystyle {\begin{matrix}{}\\{\color {Red}{\ce {R}}}{-}{\color {Blue}{\ce {X}}}+{\color {Green}{\ce {R}}'}{-}{\ce {Zn}}{\color {Magenta}{\ce {X}}'}\ {\ce {->[{\ce {PdL}}_{n}{\t…

Evidence: 39 • authority: 80

Stereospecific Iron-Catalyzed Carbon(sp2)Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides

Evidence: 36 • authority: 72

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: R − M + R ′ X ⟶ R − R ′ + MX {\displaystyle {\ce {R-M + R'X -> R-R' + MX}}} R, R' = organic fragments, usually aryl; M = main group center such as Li or Mg; X = halide These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palla…

Evidence: 36 • authority: 72

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon–carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed cross coupling reactions. Broadly speaking, two types of coup…

Evidence: 30 • authority: 72

Decarboxylative cross coupling reactions are chemical reactions in which a carboxylic acid is reacted with an organic halide to form a new carbon-carbon bond, concomitant with loss of CO2. Aryl and alkyl halides participate. Metal catalyst, base, and oxidant are required. A significant advantage of this reaction is that it uses relatively inexpensive carboxylic acids (or their salts) and is far less air and moisture sensitive in comparison to typical cross-coupling organometallic reagents. Furthermore, the carboxylic acid moiety is a common feature of natural products and can also be prepared by relatively benign air oxidations. Additional benefits include the broad tolerance of functional…

Evidence: 29 • authority: 92

Beyond traditional defunctionalized cross-coupling reaction: scope, limitations, practicability & future prospects of recent electrochemical methodologies.. Cross-coupling reactions are the most reliable techniques in organic synthesis for constructing various C-C and C-heteroatom bonds, enabling the formation of complex molecular scaffolds with significant chemical and physical properties and their diverse applications. More specifically, defunctionalized cross-coupling strategies have attracted significant research interest due to their inherent advantages, including a broader substrate scope, elimination of prior pre-functionalization steps, and improved product yields compared to tr…

Evidence: 21 • authority: 72

Organogermanium compounds in cross-coupling reactions refers to a type of cross-coupling reaction where one of the coupling partners is an organogermanium compound. Usually these reactions are catalyzed by transition metal complexes.