Catalytic cycle — Suzuki–Miyaura cross-coupling
The four-corner palladium cycle: oxidative addition of the aryl halide, base-driven exchange to the hydroxo complex, transmetalation from the activated boronate, and reductive elimination that releases the biaryl and regenerates Pd(0).
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{
"nodes": [
{ "id": "precat", "type": "gear", "label": "Pd loading T(Pd0+PdX+PdAr+PdOH) = 0.02 mM", "x": 40, "y": 40, "width": 150, "height": 104, "fill": "#f1f5f9", "stroke": "#475569" },
{ "id": "pd0", "type": "gear", "label": "Pd(0)L₂ — active catalyst", "x": 215, "y": 40, "width": 150, "height": 104, "fill": "#fef3c7", "stroke": "#a16207", "bold": true },
{ "id": "arpdx", "type": "hexagon", "label": "Ar–Pd(II)–Br", "x": 565, "y": 40, "width": 150, "height": 104, "fill": "#dbeafe", "stroke": "#1d4ed8", "bold": true },
{ "id": "arx", "type": "hexagon", "label": "Ar–Br aryl bromide", "x": 740, "y": 40, "width": 150, "height": 104, "fill": "#dbeafe", "stroke": "#1d4ed8" },
{ "id": "biaryl", "type": "flask", "label": "Ar–Ar′ biaryl product", "x": 40, "y": 200, "width": 150, "height": 104, "fill": "#dcfce7", "stroke": "#15803d", "bold": true },
{ "id": "base", "type": "flask", "label": "Base — K₂CO₃ (aq)", "x": 740, "y": 200, "width": 150, "height": 104, "fill": "#ede9fe", "stroke": "#6d28d9" },
{ "id": "turnover", "type": "gauge-chart", "label": "Turnover: ss(Pd0) = 0.02 mM · ss(ArAr) = 1.0 mM", "x": 40, "y": 360, "width": 150, "height": 104, "fill": "#e0f2fe", "stroke": "#0369a1" },
{ "id": "arpdar", "type": "hexagon", "label": "Ar–Pd(II)–Ar′", "x": 215, "y": 360, "width": 150, "height": 104, "fill": "#dbeafe", "stroke": "#1d4ed8", "bold": true },
{ "id": "arpdoh", "type": "hexagon", "label": "Ar–Pd(II)–OH", "x": 565, "y": 360, "width": 150, "height": 104, "fill": "#dbeafe", "stroke": "#1d4ed8" },
{ "id": "boronic", "type": "hexagon", "label": "Ar′–B(OH)₂ boronic acid", "x": 740, "y": 360, "width": 150, "height": 104, "fill": "#ede9fe", "stroke": "#6d28d9" },
{ "id": "ligand", "type": "sphere", "label": "Phosphine ligand (SPhos)", "x": 215, "y": 520, "width": 150, "height": 104, "fill": "#f1f5f9", "stroke": "#475569" },
{ "id": "byprod", "type": "bucket", "label": "Boron by-product — B(OH)₃", "x": 565, "y": 520, "width": 150, "height": 104, "fill": "#fee2e2", "stroke": "#b91c1c" },
{ "id": "boronate", "type": "ellipse", "label": "Boronate [Ar′B(OH)₃]⁻", "x": 740, "y": 520, "width": 150, "height": 104, "fill": "#ede9fe", "stroke": "#6d28d9" }
],
"edges": [
{ "id": "e1", "source": "precat", "target": "pd0", "label": "reduced in situ", "style": "dashed" },
{ "id": "e2", "source": "arx", "target": "pd0", "label": "Ar–Br adds to Pd(0)" },
{ "id": "e3", "source": "pd0", "target": "arpdx", "label": "oxidative addition", "thickness": 2.5 },
{ "id": "e4", "source": "arpdx", "target": "arpdoh", "label": "Br⁻ / OH⁻ exchange", "thickness": 2.5 },
{ "id": "e5", "source": "base", "target": "arpdoh", "label": "OH⁻", "style": "dashed" },
{ "id": "e6", "source": "boronic", "target": "boronate", "label": "activated by base" },
{ "id": "e7", "source": "base", "target": "boronate", "label": "OH⁻", "style": "dashed" },
{ "id": "e8", "source": "arpdoh", "target": "arpdar", "label": "transmetalation", "thickness": 2.5 },
{ "id": "e9", "source": "boronate", "target": "arpdoh", "label": "delivers Ar′ to Pd" },
{ "id": "e10", "source": "arpdar", "target": "pd0", "label": "reductive elimination", "thickness": 2.5 },
{ "id": "e11", "source": "pd0", "target": "biaryl", "label": "Ar–Ar′ released", "thickness": 2.5 },
{ "id": "e12", "source": "boronate", "target": "byprod", "label": "boric acid released", "style": "dashed" },
{ "id": "e13", "source": "ligand", "target": "pd0", "label": "stabilises Pd(0)", "style": "dashed" },
{ "id": "e14", "source": "pd0", "target": "turnover", "label": "TON / TOF", "style": "dashed" }
]
}