--- title: "Negishi coupling Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/cycle-negishi/ description: "Negishi coupling template: Catalytic cycle of the Negishi coupling: oxidative addition of R¹–X to L₂Pd(0), transmetalation from R²ZnX with loss of ZnX₂, and…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/) › Negishi coupling [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/)Premium # Negishi coupling template ![Negishi coupling template: Catalytic cycle of the Negishi coupling: oxidative addition of R¹–X to L₂Pd(0), transmetalation from R²ZnX with loss of ZnX₂, and reductive elimination of R¹–R²; key step: making the organozinc from an organolithium and ZnCl₂.](https://www.moldraw.com/templates/cycle-negishi.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 Negishi coupling: oxidative addition of R¹–X to L₂Pd(0), transmetalation from R²ZnX with loss of ZnX₂, and reductive elimination of R¹–R²; key step: making the organozinc from an organolithium and ZnCl₂. ## What the template shows - Organozinc reagents transmetalate to palladium (or nickel) - Overall: R¹–X + R²–ZnX → R¹–R² + ZnX₂ (cat. Pd(0)L₂ or Ni) - no base needed - Organozinc reagents are reactive enough to transmetalate without a base, yet tolerate esters, nitriles and ketones. - They are moisture and air sensitive, so the reaction is run under inert gas. - Couples sp³, sp² and sp carbons; Ni catalysts extend it to alkyl halides. - Negishi shared the 2010 Nobel Prize with Heck and Suzuki. - Key step: making the organozinc reagent - Organozinc halides are often made by transmetalation: the C–Li bond electrons form the C–Zn bond and chloride leaves zinc (they can also be made directly from R–X and activated zinc). - L = phosphine (e.g. PPh₃); ligands are named in the captions, not drawn · every part of this figure is editable Drawn with 17 atoms, 6 arrows, 67 shapes – every one editable in MolDraw. ## Sources - [Negishi, Acc. Chem. Res. 1982, 15, 340](https://doi.org/10.1021/ar00083a001) Review - [Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books 2010](https://openlibrary.org/isbn/9781891389535) 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 Negishi coupling template free? You can preview the Negishi 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 Negishi 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? The active catalyst, each intermediate around the cycle, the substrates that enter and the products that leave, with each elementary step named on its arrow. ## More catalytic cycles templates [**Suzuki–Miyaura coupling**Free · Catalytic cycles](https://www.moldraw.com/templates/cycle-suzuki-miyaura/)[**Mizoroki–Heck reaction**Free · Catalytic cycles](https://www.moldraw.com/templates/cycle-mizoroki-heck/)[**Olefin metathesis (Chauvin mechanism)**Free · Catalytic cycles](https://www.moldraw.com/templates/cycle-olefin-metathesis/)[**Buchwald–Hartwig amination**Premium · Catalytic cycles](https://www.moldraw.com/templates/cycle-buchwald-hartwig/)[**Sonogashira coupling**Premium · Catalytic cycles](https://www.moldraw.com/templates/cycle-sonogashira/)[**Stille coupling**Premium · Catalytic cycles](https://www.moldraw.com/templates/cycle-stille/)[**Wilkinson's catalyst: alkene hydrogenation**Premium · Catalytic cycles](https://www.moldraw.com/templates/cycle-wilkinson-hydrogenation/)[**Wacker oxidation**Premium · Catalytic cycles](https://www.moldraw.com/templates/cycle-wacker-oxidation/) ## Related pages [**All Catalytic cycles templates**10 templates](https://www.moldraw.com/templates/catalytic-cycles/)[**All chemistry templates**370 templates in 29 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 370 templates - Export the 291 premium templates as PNG, SVG or PDF - AI chemistry assistant - Structure scanning from images - Cloud save and teaching slides [See Pro plans](https://www.moldraw.com/pricing) Free templates stay free. 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