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. 2019 Oct 31;58(51):18619–18626. doi: 10.1002/anie.201910169

Scheme 6.

Scheme 6

Stereocontrolled construction of triarylethylenes Z ‐ and E ‐29 from a single precursor (E ‐23). Isomerisation reactions were performed on the a 0.1 mmol scale under standard conditions. Reagents and conditions: a) styrenyl BPin (1.0 equiv), aryl bromide (1.05 equiv), Pd(OAc)2 (5 mol %), SPhos (10 mol %), K3PO4 (3.0 equiv), H2O (5 equiv), 1,4‐dioxane, 80 °C, 4 h; b) styrenyl silane (1.0 equiv), NIS (1.2 equiv), MeCN, rt, 16 h; then styrenyl iodide (1.0 equiv), arylBPin (1.05 equiv), Pd(OAc)2 (5 mol %), SPhos (10 mol %), K3PO4 (3.0 equiv), H2O (5.0 equiv), 1,4‐dioxane, 80 °C, 4 h; c) reactions performed using thioxanthone as the catalyst.