--- title: "Kumada coupling Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/cycle-kumada/ description: "Kumada coupling template: Catalytic cycle of the Kumada–Tamao–Corriu coupling with a Ni(dppp) catalyst: oxidative addition of R¹–X to Ni(0), transmetalation…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/) › Kumada coupling [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/)Premium # Kumada coupling template ![Kumada coupling template: Catalytic cycle of the Kumada–Tamao–Corriu coupling with a Ni(dppp) catalyst: oxidative addition of R¹–X to Ni(0), transmetalation from R²MgX with loss of MgX₂, and reductive elimination of R¹–R²; key step: four-centre transmetalation from the Grignard reagent.](https://www.moldraw.com/templates/cycle-kumada.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). Catalytic cycle of the Kumada–Tamao–Corriu coupling with a Ni(dppp) catalyst: oxidative addition of R¹–X to Ni(0), transmetalation from R²MgX with loss of MgX₂, and reductive elimination of R¹–R²; key step: four-centre transmetalation from the Grignard reagent. ## What the template shows - Ni- (or Pd-) catalysed cross-coupling of an organic halide with a Grignard reagent - Overall: R¹–X + R²–MgX → R¹–R² + MgX₂ (cat. NiCl₂(dppp) or Pd(PPh₃)₄, Et₂O or THF, rt) - L₂ = dppp (cis-chelating) - The first catalytic cross-coupling (Tamao, Sumitani & Kumada; Corriu & Masse, both 1972): cheap Ni catalysts and Grignard reagents used directly. - The precatalyst NiCl₂(dppp) is reduced to Ni(0) by two equivalents of R²MgX (releasing a little R²–R²). - Grignard reagents are strong bases and nucleophiles, so esters, ketones, nitriles and OH/NH groups are not tolerated (Negishi and Suzuki couplings are milder). - Ni couples aryl chlorides and vinyl halides well; the cis-chelating dppp ligand speeds reductive elimination. - Key step: transmetalation from the Grignard reagent - Drawn as a four-centre exchange (simplified): the C–Mg bond electrons form the new Ni–C bond, bromide leaves nickel and its lone pair binds magnesium, so MgBr₂ is released. - L₂ = dppp (Ph₂P(CH₂)₃PPh₂), named in the captions, not drawn · every part of this figure is editable Drawn with 19 atoms, 7 arrows, 67 shapes – every one editable in MolDraw. ## Sources - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005, Kumada cross-coupling](https://openlibrary.org/isbn/9780124297852) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 40](https://openlibrary.org/isbn/9780199270293) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Kumada coupling template free? You can preview the Kumada coupling template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Kumada coupling template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### What does a catalytic cycle template show? 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