--- title: "Sonogashira coupling Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/cycle-sonogashira/ description: "Sonogashira coupling template: Pd and Cu catalytic cycles of the Sonogashira coupling: oxidative addition of R¹–X, transmetalation from the copper acetylide…" 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/) › Sonogashira coupling [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/)Premium # Sonogashira coupling template ![Sonogashira coupling template: Pd and Cu catalytic cycles of the Sonogashira coupling: oxidative addition of R¹–X, transmetalation from the copper acetylide and reductive elimination of R¹–C≡C–R²; CuX plus amine base turns the terminal alkyne into Cu–C≡CR²; key step: the amine deprotonates the alkyne.](https://www.moldraw.com/templates/cycle-sonogashira.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). Pd and Cu catalytic cycles of the Sonogashira coupling: oxidative addition of R¹–X, transmetalation from the copper acetylide and reductive elimination of R¹–C≡C–R²; CuX plus amine base turns the terminal alkyne into Cu–C≡CR²; key step: the amine deprotonates the alkyne. ## What the template shows - A Pd cycle and a Cu cycle: the copper acetylide carries the alkyne to palladium - Overall: R¹–X + H–C≡C–R² → R¹–C≡C–R² (cat. Pd(0)L₂, cat. CuI, Et₃N) - Transmetalation (Pd cycle, step 2) - C≡C–R² moves from Cu to Pd - and CuX is released - π-Coordination of the alkyne to Cu(I) makes its C–H acidic enough for the amine; the acetylide joins the Pd cycle at transmetalation (step 2) and CuX is released. - Two cycles: Pd does the oxidative addition and the C–C bond formation; Cu(I) activates the alkyne. - The amine (Et₃N, iPr₂NH) is the base and often the solvent. - Copper-free versions avoid Glaser homocoupling of the alkyne (R²C≡C–C≡CR²), a side reaction promoted by Cu and O₂. - Works for aryl and vinyl halides; reactivity I > Br ≫ Cl. - Key step: the amine deprotonates the alkyne - Shown without copper for clarity: the N lone pair takes the alkyne proton and the C–H electrons stay on carbon as the acetylide, which copper captures as Cu–C≡CR². - terminal alkyne - L = phosphine (e.g. PPh₃); ligands are named in the captions, not drawn · every part of this figure is editable Drawn with 36 atoms, 7 arrows, 83 shapes – every one editable in MolDraw. ## Sources - [Chinchilla & Nájera, Chem. Rev. 2007, 107, 874](https://doi.org/10.1021/cr050992x) 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 Sonogashira coupling template free? You can preview the Sonogashira 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 Sonogashira 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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