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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 236. Syntheses of Unsubstituted Trichalcogenasumanenes from Triphenylene-Based Precursors.

Scheme 236

Reagents and conditions: (a)435m-CPBA, TfOH, DCM, 0 °C to rt, 12 h; (b) AcSK, CuCl2, DMSO, 110 °C, 48 h; (c) S8 powder, Cs2CO3, DMSO, 140 °C, 12 h; (d) S8 powder, Cs2CO3, DMSO, 80 °C, 12 h; (e) Cu, tetralin, 200 °C, 1–2 h; (f) Se powder, t-BuOK, DMSO, 70 °C, 24 h; (g)436 Te powder, 2-picoline, DMSO, 125 °C, 12 h; (h)438 (1) HCl, NaNO2, H2O, 0 °C, (2) KSCN, FeCl3, 0 °C, then rt, 1 h; (i) Na2S·9H2O, EtOH/H2O (2/1), reflux, overnight; (j) PdCl2 (90 mol %), DMSO, 120 °C, 24 h.