Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C1COCC1>[CH3:18][Si:19]([C:22]#[C:23][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1)([CH3:21])[CH3:20]4-Bromobenzo[c][1,2,5]thiadiazole (0.378 g, 1.76×10−3 mol), Pd(PPh3)4 (0.125 g, 1.68×10−4 mol), CuI (0.014 g, 7.4×10−5 mol), THF (20 ml), diisopropylamine (1.00 ml), and (trimethylsilyl)acetylene (1.00 ml, 7.1×10−3 mol) were added to a 50-ml Schlenk tube. N2 was bubbled through the mixture for 5 min, following which the reaction was stirred at 45° C. for 20 h. After cooling, the solvent was evaporated and the residue was chromatographed on silica gel using 1:1 hexanes:CHCl3 as the eluent. Yield=0.398 g (97.3% based on 0.378 g of 4-bromobenzothiadiazole). 1H NMR (500 MHz, CDCl3): δ 7.88 (m, 1H, Ph-H), 7.67 (m, 1H, Ph-H), 7.45 (m, 1H, Ph-H), 0.33 (s, 9H, —Si—CH3).
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