10.1002/adsc.201900603
Advanced Synthesis & Catalysis
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3H). 13C NMR (CDCl3, 100 MHz): δ 147.0, 132.3, 131.8,
130.4, 129.2, 128.6, 123.8, 122.1, 94.6, 87.6. HRMS (EI)
Calcd for C14H10NO2 [M+H]+, 224.0706; found, 22.0713.
White solid (84 mg, 79%). mp 82–83 C. H NMR (400
MHz, CDCl3): δ 7.62–7.55 (m, 2H), 7.50 (d, J = 8.4 Hz,
2H), 7.43–7.33 (m, 5H). 13C NMR (100 MHz, CDCl3): δ
134.4, 132.9, 131.7, 128.8, 128.6, 128.5, 123.1, 121.9, 90.5,
88.4. HRMS (EI) Calcd for C14H10Cl [M+H]+, 213.0466;
found, 213.0473.
1-(Phenylethynyl)-4-(trifluoromethyl)benzene (2f)
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White solid (89 mg, 72%). mp 103–104 C. H NMR (400
MHz, CDCl3): δ 7.70–7.62 (m, 4H), 7.59 (dd, J = 6.4, 2.8
Hz, 2H), 7.45–7.35 (m, 3H). 13C NMR (100 MHz, CDCl3):
1-bromo-4-(phenylethynyl)benzene (2k).
δ 132.0, 131.9, 129.0, 128.6, 125.5, 125.44, 125.41, 125.36, White solid (105 mg, 82%). mp 82–83 C.1H NMR (400
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122.8, 91.9, 88.1. HRMS (EI) Calcd for C15H10F3 [M+H]+,
247.0724; found, 247.0718.
MHz, CDCl3): δ 7.57–7.46 (m, 4H), 7.42–7.31 (m, 5H).
13C NMR (100 MHz, CDCl3): δ 133.2, 131.8, 131.7, 128.7,
128.5, 123.1, 122.6, 122.4, 90.7, 88.5. HRMS (EI) Calcd
for C14H10Br [M+H]+, 256.9960; found, 256.9966.
1-(4-(phenylethynyl)phenyl)ethan-1-one (2g, 3m).
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1-(phenylethynyl)naphthalene (2o).
Yellow solid (88 mg, 75%). mp 95–96 C. H NMR (400
MHz, CDCl3): δ 7.98–7.92 (m, 2 H), 7.62 (d, J = 8.4 Hz, 2
H), 7.56 (dd, J = 6.8, 3.2 Hz, 2 H), 7.40–7.35 (m, 3 H),
2.63 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 197.3, 136.3,
131.8, 131.7, 128.9, 128.5, 128.4, 128.2, 122.6, 92.7, 88.5,
26.6. HRMS (EI) Calcd for C16H13O [M+H]+, 221.0961;
found, 221.0964.
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White solid (87 mg, 76%). mp 116–119 C. H NMR (400
MHz, CDCl3): δ 8.55 (d, J = 8.4 Hz, 1H), 7.89 (dt, J = 21.2,
11.4 Hz, 3H), 7.80–7.66 (m, 3H), 7.60 (dd, J = 14.4, 7.2
Hz, 1H), 7.56–7.37 (m, 4H). 13C NMR (100 MHz, CDCl3):
δ 133.8, 133.7, 132.1, 130.8, 129.2, 128.9, 128.8, 128.7,
127.2, 126.9, 126.7, 125.7, 123.9, 121.4, 94.8, 88.0.
HRMS (EI) Calcd for C18H13 [M+H]+, 229.1012; found,
229.1002.
4-(phenylethynyl)benzonitrile (2h, 3e).
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Yellow solid (71 mg, 70%). mp 109–111 C. H NMR
(400 MHz, CDCl3): δ 7.66 (d, J = 8.4 Hz, 2 H), 7.62 (d, J =
8.4 Hz, 2 H), 7.58–7.53 (m, 2 H), 7.40 (dd, J = 5.2, 2.0 Hz,
3 H). 13C NMR (100 MHz, CDCl3): δ 132.08, 132.04,
131.7, 129.1, 128.6, 128.3, 122.3, 118.6, 111.6, 93.8, 87.7.
HRMS (EI) Calcd for C15H10N [M+H]+, 204.0808; found,
204.0812.
3-(phenylethynyl)pyridine (2p).
White solid (59 mg, 66%). mp 48–49 C.1H NMR (400
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MHz, CDCl3): δ 8.78 (s, 1 H), 8.56 (d, J = 4.0 Hz, 1 H),
7.83 (d, J = 8.0 Hz, 1 H), 7.61–7.53 (m, 2 H), 7.42–7.36
(m, 3 H), 7.30 (ddd, J = 8.0, 4.8, 1.0 Hz, 1 H). 13C NMR
(100 MHz, CDCl3): δ 152.3, 148.5, 138.4, 128.8, 128.6,
123.1, 122.6, 92.7, 85.8. HRMS (EI) Calcd for C13H10N
[M+H]+, 180.0808; found, 180.0800.
4-(phenylethynyl)benzaldehyde (2i, 3n).
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Yellow solid (68 mg, 66%). mp 98–99 C. H NMR (400
MHz, CDCl3): δ 10.05 (s, 1 H), 7.88 (d, J = 8.4 Hz, 2H),
7.70 (d, J = 8.0 Hz, 2 H), 7.60–7.50 (m, 2 H), 7.44–7.36
(m, 3 H). 13C NMR (100 MHz, CDCl3): δ 192.19, 192.17,
4,6-dimethoxy-2-(phenylethynyl)pyrimidine (2q).
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Yellow solid (76 mg, 63%). mp 133–135 C. H NMR
136.3, 132.9, 132.5, 130.5, 130.3, 129.6, 129.2, 123.3, 94.2, (400 MHz, CDCl3): δ 7.72–7.66 (m, 2 H), 7.44–7.36 (m, 3
89.2. HRMS (EI) Calcd for C15H11O [M+H]+, 207.0804;
found, 207.0813.
H), 6.04 (s, 1 H), 4.02 (s, 6 H). 13C NMR (100 MHz,
CDCl3): δ 171.2, 151.2, 132.7, 129.5, 128.5, 121.5, 90.1,
88.1, 86.6, 54.4. HRMS (EI) Calcd for C14H13N2O2
[M+H]+, 241.0972; found, 241.0965.
1-methyl-3-(phenylethynyl)benzene (2l, 3h).
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3-methoxy-6-(phenylethynyl)pyridazine (2r).
Yellow oil (79 mg, 82%). H NMR (400 MHz, CDCl3): δ
7.62–7.57 (m, 2H), 7.45–7.36 (m, 5 H), 7.30 (td, J = 7.6,
1.6 Hz, 1 H), 7.21 (d, J = 7.6 Hz, 1 H), 2.42 (s, 3 H). 13C
NMR (100 MHz, CDCl3): δ 138.2, 132.2, 131.5, 129.2,
128.7, 128.6, 128.4, 128.3, 128.2, 123.5, 123.1, 89.6, 89.1,
21.2. HRMS (EI) Calcd for C15H13 [M+H]+, 193.1012;
found, 193.1019.
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Yellow solid (61 mg, 58%). mp 98–100 C.1H NMR (400
MHz, CDCl3): δ 7.63–7.56 (m, 2 H), 7.50 (d, J = 9.2 Hz, 1
H), 7.36 (dd, J = 5.4, 2.0 Hz, 3 H), 6.93 (d, J = 9.2 Hz, 1
H), 4.16 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 163.4,
143.6, 132.3, 132.1, 129.2, 128.3, 121.9, 116.7, 92.1, 85.6,
55.1. HRMS (EI) Calcd for C13H11N2O [M+H]+, 211.0866;
found, 211.0858.
1-methyl-2-(phenylethynyl)benzene (2m, 3j).
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4-(phenylethynyl)-1,1'-biphenyl (3c).
Colorless oil (69 mg, 72%). H NMR (400 MHz, CDCl3):
δ 7.64–7.59 (m, 2 H), 7.57 (s, 1 H), 7.39 (dd, J = 9.2, 7.2
Hz, 3 H), 7.31–7.26 (m, 2 H), 7.24 (dd, J = 8.0, 4.4 Hz, 1
H), 2.58 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 140.2,
131.8, 131.6, 129.6, 128.4, 128.3, 128.2, 125.5, 123.6,
123.2, 93.4, 88.5, 20.8. HRMS (EI) Calcd for C15H13
[M+H]+, 193.1012; found, 193.1007.
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White solid (107 mg, 84%). mp 163–166 C. H NMR
(400 MHz, CDCl3): δ 7.64 (dt, J = 8.0, 6.0 Hz, 8H), 7.51 (t,
J = 7.6 Hz, 2H), 7.46–7.35 (m, 4H). 13C NMR (100 MHz,
CDCl3): δ 141.4, 140.8, 132.5, 132.1, 129.3, 128.8, 128.7,
128.1, 127.5, 123.8, 122.7, 90.6, 89.8. HRMS (EI) Calcd
for C20H15 [M+H]+, 255.1168; found, 255.1159.
1,3-dimethyl-2-(phenylethynyl)benzene (2n, 3l).
1-methoxy-3-(phenylethynyl)benzene (3g).
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Colorless oil (65 mg, 63%). H NMR (400 MHz, CDCl3):
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δ 7.58 (dd, J = 6.4, 2.0 Hz, 2 H), 7.43–7.32 (m, 3 H), 7.19–
7.15 (m, 1 H), 7.12 (dd, J = 7.6, 2.4 Hz, 2 H), 2.58 (s, 6 H).
13C NMR (100 MHz, CDCl3): δ 140.3, 131.5, 128.4, 128.2,
127.8, 126.6, 123.9, 123.1, 97.9, 87.2, 21.2. HRMS (EI)
Calcd for C15H13 [M+H]+, 207.1168; found, 207.1161.
Yellow solid (75 mg, 72%). mp 77–79 C. H NMR (400
MHz, CDCl3): δ 7.63–7.55 (m, 2 H), 7.40–7.36 (m, 3 H),
7.30 (dd, J = 8.4, 7.6 Hz, 1 H), 7.18 (d, J = 7.6 Hz, 1 H),
7.12 (dd, J = 2.8, 1.4 Hz, 1 H), 6.94 (ddd, J = 8.2, 2.8, 1.0
Hz, 1 H), 3.85 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ
159.3, 131.6, 129.5, 128.41, 128.36, 124.3, 124.2, 123.1,
116.3, 115.1, 89.3, 89.1, 55.3. HRMS (EI) Calcd for
C15H13O [M+H]+, 209.0961; found, 209.0954.
1-chloro-4-(phenylethynyl)benzene (2j).
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