Cesium fluoride → 5-(2-Tetracenyl)-2,2'-bithiophene

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (21 mg, 0.023 mmol, 1.5%), CsF (511 mg, 3.37 mmol, 2.2 eq), dioxane (25 mL), 2-chlorotetracene (403 mg, 1.53 mmol), 5-tri-n-butylstannyl-2,2′-bithiophene (766 mg, 1.68 mmol), P(t-Bu)3 (0.26 mL, 0.090 mmol, 6%) were mixed, bubbled with N2 via cannula for 30 min, and then heated at 100° C. for 16 h. An additional charge of 10 mg of Pd[P(t-Bu)3]2 and 140 mg 5-tri-n-butylstannyl-2,2′-bithiophene and heated at 100° C. for another 24 h. Cooled the mixture and poured on a glass filter frit (10–15 μm pores) and washed the reddish crude with Et2O, water, and air-dried. Gradient sublimation at a source temperature of 250–270° C. afforded 443 mg (74%, on 2-chlorotetracene) of bright orange-red product. DSC: 341° C. (mp, ΔH=87 Jg−1). EIMS: 392 ([M]+, 100%), 196 ([M]2+, 20%). Anal. Calcd. for C26H16S2: C, 79.6; H, 4.1. Found: C, 80.0; H, 4.34.

Provenance & Evidence