反応 #977788

反応方程式

CsF

2-chlorotetracene

5-tri-n-butylstannyl-2,2′-bithiophene

P(t-Bu)3

→

5-(2-tetracenyl)-2,2′-bithiophene

溶媒

dioxane

反応条件

後処理

1. 1
   その他bubbled with N2 via cannula for 30 min
2. 2
   workup.ADDITIONAn additional charge of 10 mg of Pd[P(t-Bu)3]2 and 140 mg 5-tri-n-butylstannyl-2,2′-bithiophene
3. 3
   温度heated at 100° C. for another 24 h
4. 4
   温度Cooled the mixture
5. 5
   workup.ADDITIONpoured on a glass
6. 6
   ろ過filter frit (10–15 μm pores)
7. 7
   洗浄washed the reddish crude with Et2O, water
8. 8
   その他air-dried
9. 9
   その他Gradient sublimation at a source temperature of 250–270° C. afforded 443 mg (74%, on 2-chlorotetracene) of bright orange-red product
10. 10
    その他341° C. (mp, ΔH=87 Jg−1)

実験手順

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.

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