--- title: "Buchwald–Hartwig amination Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/cycle-buchwald-hartwig/ description: "Buchwald–Hartwig amination template: Catalytic cycle of the Buchwald–Hartwig amination: oxidative addition of Ar–X to LPd(0), amine binding, deprotonation by…" 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/) › Buchwald–Hartwig amination [Catalytic cycles](https://www.moldraw.com/templates/catalytic-cycles/)Premium # Buchwald–Hartwig amination template ![Buchwald–Hartwig amination template: Catalytic cycle of the Buchwald–Hartwig amination: oxidative addition of Ar–X to LPd(0), amine binding, deprotonation by NaOtBu to the Pd amido complex and C–N reductive elimination; key step: tert-butoxide deprotonates the Pd-bound amine.](https://www.moldraw.com/templates/cycle-buchwald-hartwig.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 Buchwald–Hartwig amination: oxidative addition of Ar–X to LPd(0), amine binding, deprotonation by NaOtBu to the Pd amido complex and C–N reductive elimination; key step: tert-butoxide deprotonates the Pd-bound amine. ## What the template shows - Pd-catalysed C–N coupling of an aryl halide with an amine and a strong base - Overall: Ar–X + HNR¹R² + NaOtBu → Ar–NR¹R² + tBuOH + NaX (cat. LPd(0)) - Pd(0), bulky phosphine L - [LPd(Ar)(HNR¹R²)]⁺ - Pd(II), amine complex - Pd(II), amido complex - C–N bond formation - Bulky, electron-rich ligands (biaryl phosphines such as XPhos, or BINAP, dppf) favour the monoligated LPd(0) and fast reductive elimination. - A strong base (NaOtBu, LiHMDS) or a weaker one (Cs₂CO₃, K₃PO₄) for sensitive substrates. - C–N reductive elimination competes with β-hydride elimination from the amido group, which gives arene and imine. - Pd(0)/Pd(II) throughout, as in the C–C couplings. - Key step: deprotonation of the bound amine - Binding to Pd(II) makes the N–H proton acidic enough for tert-butoxide to remove; the N–H electrons stay on nitrogen as the lone pair of the amido ligand. - tert-butoxide - amine complex - amido complex - L = phosphine; the charges on the amine complex are formal (the complex is a cation) · every part of this figure is editable Drawn with 29 atoms, 7 arrows, 99 shapes – every one editable in MolDraw. ## Sources - [Ruiz-Castillo & Buchwald, Chem. Rev. 2016, 116, 12564](https://doi.org/10.1021/acs.chemrev.6b00512) 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 Buchwald–Hartwig amination template free? You can preview the Buchwald–Hartwig amination 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 Buchwald–Hartwig amination 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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