(vs), 1093(s), 1006(m), 931(s), 854(m), 810(m), 729(w),
682(m).
(m), 1261(m), 1228(m), 1156(m), 1103(s), 1112(s), 1028(m),
910(w), 754(vs), 690(vs). ESI-MS: calcd for C20H27N (M + 1)
282.21, found: 282.33.
General procedure for the catalytic reactions. All the ex-
periments were carried out under air atmosphere. A mixture of
complex 1 (14.8 mg, 0.038 mmol, 1.9 mmol%), phenylacetylene
(2.4 mmol), aldehyde (2 mmol) and amine (2.2 mmol) in
solvent (2 mL) was stirred at room temperature. When the reac-
tion was stirred for a long enough time (monitored by TLC), the
reaction mixture was concentrated under reduced pressure.
The residue was purified by flash chromatography to afford the
product.
1-Cyclohexyl-N,N-diethyl-3-phenylprop-2-yn-1-amine. Pale
yellow oil, 1H NMR (CDCl3, 500 MHz, ppm): δ 0.89–0.94
(m, 1H), 1.08 (t, J = 7.0 Hz, 6H), 1.18–1.32 (m, 4H), 1.58–1.60
(m, 1H), 1.70–1.71 (m, 1H), 1.75–1.80 (m, 3H), 2.12–2.14
(m, 2H), 2.43–2.47 (m, 2H), 2.65–2.72 (m, 2H), 3.32 (d, J =
10.0 Hz, 1H), 7.29–7.34 (m, 3H), 7.43–7.45 (m, 2H). 13C NMR
(CDCl3, 125 MHz): δ 13.77, 26.05, 26.29, 26.83, 30.70, 31.40,
40.31, 44.85, 59.38, 85.28, 88.39, 123.90, 127.55, 128.16,
131.66. IR (KBr pellet, cm−1): 3080(w), 3057(w), 2968(vs),
2924(vs), 2851(vs), 1598(m), 1489(s), 1468(m), 1448(s), 1381
(s), 1293(m), 1260(m), 1197(m), 1169(s), 1111(m), 1068(s),
1045(s), 981(m), 911(w), 754(vs), 691(s). ESI-MS: calcd for
C19H27N (M + 1) 270.21, found: 270.33.
1-Cyclopentyl-N,N-diethyl-3-phenylprop-2-yn-1-amine. Pale
yellow oil, 1H NMR (CDCl3, 500 MHz, ppm): δ 1.10 (t, J = 6.8
Hz, 6H), 1.44–1.51 (m, 2H), 1.55–1.60 (m, 2H), 1.61–1.68
(m, 2H), 1.79–1.81 (m, 1H), 1.90–1.96 (m, 1H), 2.18–2.25
(m, 1H), 2.45–2.49 (m, 2H), 2.72–2.76 (m, 2H), 3.37 (d, J =
10.0 Hz, 1H), 7.30–7.33 (m, 3H), 7.42–7.44 (m, 2H). 13C NMR
(CDCl3, 125 MHz): δ 13.84, 25.20, 25.38, 30.60, 31.02, 43.22,
44.95, 58.72, 84.45, 89.06, 123.94, 127.57, 128.18, 131.69. IR
(KBr pellet, cm−1): 3080(w), 3056(w), 2962(vs), 2868(s), 2816
(s), 1598(s), 1489(s), 1470(s), 1444(s), 1380(s), 1295(m), 1255
(s), 1196(s), 1115(s), 1068(s), 985(m), 911(w), 754(vs), 690(s).
ESI-MS: calcd for C18H25N (M + 1) 256.20, found: 256.25.
2-(1-Cyclohexyl-3-phenylprop-2-ynyl)isoindoline. Brown solid,
1H NMR (CDCl3, 500 MHz, ppm): δ 1.12–1.36 (m, 6H),
1.67–1.74 (m, 1H), 1.79–1.84 (m, 2H), 2.11 (d, J = 12.5 Hz,
1H), 2.20 (d, J = 12.5 Hz, 1H), 3.60 (d, J = 7.0 Hz, 1H), 4.16
(s, 4H), 7.21–7.25 (m, 4H), 7.28–7.29 (m, 3H), 7.40–7.41 (m,
2H). 13C NMR (CDCl3, 125 MHz): δ 26.19, 26.25, 26.75,
30.56, 30.72, 41.36, 55.37, 60.91, 87.42, 87.89, 122.41, 123.42,
126.61, 127.89, 128.22, 131.76, 140.03. IR (KBr pellet, cm−1):
3424(vs), 2916(vs), 2892(s), 2847(s), 2791(s), 1652(m), 1488
(m), 1462(m), 1443(m), 1345(w), 1302(w), 1260(m), 1126(s),
1062(m), 1026(w), 978(w), 917(w), 858(w), 747(vs), 692(s).
ESI-MS: calcd for C23H25N (M + 1) 316.20, found: 316.33.
1-(1-Cyclopentyl-3-phenylprop-2-ynyl)pyrrolidine. Pale yellow
1
oil, H NMR (CDCl3, 500 MHz, ppm): δ 0.91 (t, J = 6.5 Hz,
1H), 1.28 (s, 2H), 1.52–1.61 (m, 3H), 1.67–1.68 (m, 2H), 1.83
(s, 3H), 1.90–1.93 (m, 1H), 2.22–2.24 (m, 1H), 2.74 (s, 2H),
2.81 (s, 2H), 3.58 (s, 1H), 7.31–7.34 (m, 3H), 7.44–7.46
(m, 2H). 13C NMR (CDCl3, 125 MHz): δ 23.64, 25.46, 25.59,
30.34, 30.54, 44.07, 49.96, 60.09, 85.33, 88.13, 123.77, 127.67,
128.18, 131.74. IR (KBr pellet, cm−1): 2955(vs), 2868(s), 2805
(s), 1598(m), 1489(s), 1444(s), 1346(m), 1312(m), 1254(w),
1138(m), 1029(m), 754(vs), 690(vs). ESI-MS: calcd for
C18H23N (M + 1) 254.18, found: 254.33.
1
1-(1-Cyclohexyl-3-phenylprop-2-ynyl)indoline. Brown oil, H
NMR (CDCl3, 500 MHz, ppm): δ 0.98–1.08 (m, 1H), 1.17–1.37
(m, 4H), 1.75–1.87 (m, 4H), 2.12 (d, J = 12.5 Hz, 1H), 2.23
(d, J = 12.0 Hz, 1H), 3.00–3.06 (m, 2H), 3.48–3.54 (m, 2H),
4.17 (d, J = 10.0 Hz, 1H), 6.61 (d, J = 8.0 Hz, 1H), 6.70 (t, J =
7.0 Hz, 1H), 7.11 (t, J = 6.5 Hz, 2H), 7.27 (m, 3H), 7.34–7.35
(m, 2H). 13C NMR (CDCl3, 125 MHz): δ 26.06, 26.19, 26.68,
28.46, 30.28, 31.06, 41.15, 48.32, 55.41, 85.31, 87.11, 107.76,
117.98, 123.33, 124.47, 127.24, 127.95, 128.20, 130.16, 131.86,
151.72. IR (KBr pellet, cm−1): 3420(m), 3049(w), 2924(vs),
2850(s), 1606(s), 1487(vs), 1460(m), 1449(m), 1379(w), 1316
(w), 1252(s), 1157(m), 754(vs), 715(m), 691(s). ESI-MS: calcd
for C23H25N (M + 1) 316.20, found: 316.17.
1-(1-Cyclohexyl-3-phenylprop-2-ynyl)pyrrolidine. Pale yellow
1
oil, H NMR (CDCl3, 500 MHz, ppm): δ 1.13–1.31 (m, 6H),
1.70 (d, J = 11.0 Hz, 1H), 1.78–1.83 (m, 6H), 1.98 (d, J = 12.5
Hz, 1H), 2.11 (d, J = 13.0 Hz, 1H), 2.71 (s, 2H), 2.78 (s, 2H),
3.41 (s, 1H), 7.31–7.34 (m, 3H), 7.45–7.47 (m, 2H). 13C NMR
(CDCl3, 125 MHz): δ 23.61, 26.26, 26.75, 30.37, 30.73, 41.40,
50.03, 61.24, 85.86, 87.86, 123.71, 127.71, 128.90, 131.73. IR
(KBr pellet, cm−1): 3080(w), 3056(w), 2923(vs), 2874(s), 2851
(vs), 2806(s), 1598(m), 1489(s), 1448(s), 1348(m), 1308(m),
1217(m), 1196(m), 1129(m), 1112(s), 1069(m), 984(m), 911(m),
755(vs), 690(vs). ESI-MS: calcd for C19H25N (M + 1) 268.20,
found: 268.25.
2-(1-Cyclohexyl-3-phenylprop-2-ynyl)-1,2,3,4-tetrahydroisoqui-
noline. Yellow oil, 1H NMR (CDCl3, 500 MHz, ppm): δ
0.89–1.00 (m, 2H), 1.10–1.14 (m, 1H), 1.21–1.28 (m, 3H),
1.31–1.41 (m, 1H), 1.73–1.84 (m, 3H), 2.11 (d, J = 13.0 Hz,
1H), 2.21 (d, J = 12.0 Hz, 1H), 2.74 (d, J = 3.0 Hz, 1H),
2.95–3.00 (m, 2H), 3.40 (d, J = 7.5 Hz, 1H), 3.76 (d, J = 15.0
Hz, 1H), 3.93 (d, J = 14.5 Hz, 1H), 7.09–7.14 (m, 4H), 7.30
(s, 3H), 7.44 (d, J = 4.0 Hz, 2H). 13C NMR (CDCl3, 125 MHz):
δ 26.10, 26.34, 26.85, 29.82, 30.52, 31.45, 39.88, 47.35, 52.49,
63.81, 86.74, 86.96, 123.58, 125.55, 125.92, 126.78, 127.85,
128.27, 128.72, 131.80, 134.75, 135.72. IR (KBr pellet, cm−1):
3421(vs), 3021(w), 2922(vs), 2850(s), 1639(m), 1598(m), 1489
(s), 1446(s), 1384(w), 1318(w), 1267(m), 1130(m), 1099(m),
1038(w), 981(w), 936(w), 890(w), 754(vs), 743(vs), 690(s).
ESI-MS: calcd for C24H27N (M + 1) 330.21, found: 330.33.
1-(1-Cyclohexyl-3-phenylprop-2-ynyl)piperidine. Pale yellow
1
oil, H NMR (CDCl3, 500 MHz, ppm): δ 0.89–1.09 (m, 2H),
1.16–1.34 (m, 4H), 1.46 (d, J = 4.5 Hz, 2H), 1.58–1.63 (m, 4H),
1.69–1.71 (m, 1H), 1.77–1.80 (m, 2H), 2.06 (d, J = 13.0 Hz,
1H), 2.12 (d, J = 12.5 Hz, 1H), 2.42 (s, 2H), 2.65 (s, 2H), 3.12
(d, J = 9.5 Hz, 1H), 7.31–7.32 (m, 3H), 7.46–7.47 (m, 2H). 13C
NMR (CDCl3, 125 MHz): δ 24.75, 26.14, 26.30, 26.84, 30.49,
31.36, 39.65, 64.42, 86.23, 87.73, 123.84, 127.61, 128.18,
131.73. IR (KBr pellet, cm−1): 3056(w), 2929(vs), 2850(vs),
2801(s), 2749(m), 1598(m), 1489(s), 1444(s), 1348(m), 1317
5890 | Dalton Trans., 2012, 41, 5889–5896
This journal is © The Royal Society of Chemistry 2012