Helvetica Chimica Acta – Vol. 92 (2009)
Table 3. Recycling Experimenta)
901
Time [h]
Yield [%]b)
Cycle 1
Cycle 2
Cycle 3
8
24
40
88
85
80
a) Reaction conditions: iodoarene (1 mmol), terminal alkyne (1.2 mmol), 1 mol-% of Pd EnCatTM 30,
piperidine (2 mmol), H2O/MeCN 1 : 1 (4 ml), 408. b) GC/MS yield based on the amount of iodobenzene
used.
1-Nitro-4-(2-phenylethynyl)benzene. Pale-yellow power. M.p. 117.5 – 118.58 ([9b]: 119 – 1208).
1H-NMR: 8.22 (d, J ¼ 8.8, 2 arom. H); 7.66 (d, J ¼ 8.8, 2 arom. H); 7.57 (d, J ¼ 9.2, 2 arom. H); 7.40 –
7.37 (m, 3 arom. H). EI-MS: 223 (100, Mþ), 193 (20), 176 (60), 151 (25).
1
1-[2-(4-Nitrophenyl)ethynyl]cyclohexanol. Pale-yellow powder. M.p. 101.2 – 101.48. H-NMR: 8.18
(d, J ¼ 8.0, 2 arom. H); 7.57 (d, J ¼ 8.0, 2 arom. H); 2.03 – 1.98 (m, 2 H); 1.79 – 1.56 (m, 8 H). EI-MS: 245
(8, Mþ), 228 (35), 202 (100).
1-(Hex-1-yn-1-yl)-4-nitrobenzene. Pale-yellow oil. 1H-NMR: 8.12 (d, J ¼ 8.0, 2 arom. H); 7.48 (d, J ¼
8.0, 2 arom. H); 2.43 (t, J ¼ 8.0, CH2); 1.61 – 1.55 (m, CH2); 1.49 – 1.43 (m, CH2); 0.94 (t, J ¼ 8.0, Me). EI-
MS: 203 (66, Mþ), 188 (100), 142 (92), 128 (90), 115 (56).
1-[4-(2-Phenylethynyl)phenyl]ethanone. Colorless needles. M.p. 100.0 – 100.48 ([4b]: 95 – 968).
1H-NMR: 7.92 (d, J ¼ 8.0, 2 arom. H); 7.56 (d, J ¼ 8.0, 2 arom. H); 7.55 – 7.52 (m, 2 arom. H); 7.33 –
7.38 (m, 3 arom. H); 2.60 (s, Me). EI-MS: 220 (70, Mþ), 205 (100), 176 (40), 151 (15).
1-{4-[2-(1-Hydroxycyclohexyl)ethynyl]phenyl}ethanone. Colorless crystals. M.p. 82 – 838 ([4b]: 82 –
1
838). H-NMR: 7.90 (d, J ¼ 8.0, 2 arom. H); 7.51 (d, J ¼ 8.0, 2 arom. H); 2.60 (s, Me); 2.07 – 2.00 (m,
3 H); 1.77 – 1.57 (m, 7 H). EI-MS: 242 (55, Mþ), 199 (100), 171 (41).
1
1-[4-(Hex-1-yn-1-yl)phenyl]ethanone. Colorless oil. H-NMR: 7.86 (d, J ¼ 8.0, 1 arom. H); 7.82 (d,
J ¼ 8.0, 1 arom. H); 7.65 (d, J ¼ 8.0, 1 arom. H); 7.45 (d, J ¼ 8.0, 1 arom. H); 2.58 (s, Me); 2.31 (t, J ¼ 8.0,
CH2); 1.64 – 1.57 (m, CH2); 1.53 – 1.40 (m, CH2); 0.95 (t, J ¼ 8.0, CH2). EI-MS: 200 (27, Mþ), 185 (100),
157 (19), 129 (27), 115 (17).
1
2-(2-Phenylethynyl)thiophene. Colorless oil. H-NMR: 7.56 – 7.53 (m, 2 arom. H); 7.38 – 7.36 (m, 3
arom. H); 7.31 – 7.30 (m, 2 arom. H); 7.03 (dd, J ¼ 4.0, 8.0, 1 arom. H). EI-MS: 184 (100, Mþ), 152 (10),
139 (15).
1-[2-(2-Thienyl)ethynyl]cyclohexanol. Colorless needles. M.p. 95.5 – 96.68 ([9c]: 97 – 998). 1H-NMR:
7.23 (d, J ¼ 4.0, 1 arom. H); 7.19 (d, J ¼ 4.0, 1 arom. H); 6.96 (dd, J ¼ 4.0, 8.0, 1 arom. H); 2.04 – 1.98 (m,
3 H); 1.77 – 1.58 (m, 7 H). EI-MS: 206 (42, Mþ), 163 (100), 150 (30), 135 (41), 110 (20).
1
2-(Hex-1-yn-1-yl)thiophene. Colorless oil. H-NMR: 7.15 (d, J ¼ 4.0, 1 arom. H); 7.10 (d, J ¼ 4.0, 1
arom. H); 6.92 (dd, J ¼ 4.0, 8.0, 1 arom. H); 2.42 (t, J ¼ 8.0, CH2); 1.61 – 1.52 (m, CH2); 1.50 – 1.41 (m,
CH2); 0.88 (t, J ¼ 8.0, Me). EI-MS: 164 (64, Mþ), 149 (49), 135 (50), 121 (100).
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