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. 2021 Mar 22;11(19):11655–11662. doi: 10.1039/d1ra00534k

Synthesis of 4a–4ya.

graphic file with name d1ra00534k-u2.jpg
Entry 1, Ar = 2, Ar′ = 4b, (%)
1 1a, Ph 2a, Ph 4a, 81
2 1a, Ph 2b, 4-MeOC6H4 4b, 82
3 1a, Ph 2c, 3-MeOC6H4 4c, 80
4 1a, Ph 2d, 3,4,5-(MeO)3C6H2 4d, 78
5 1a, Ph 2e, 2,3,4-(MeO)3C6H2 4e, 72
6 1a, Ph 2f, 3,4-CH2O2C6H3 4f, 73
7 1a, Ph 2g, 4-PhC6H4 4g, 80
8 1a, Ph 2h, 3,4-(MeO)2C6H3 4h, 72
9 1a, Ph 2i, 3,4-Cl2C6H3 4i, 78
10 1a, Ph 2a, Ph 4j, 80
11 1b, 4-MeOC6H4 2a, Ph 4k, 76
12 1c, 3-MeOC6H4 2a, Ph 4l, 68
13 1d, 3-MeO-5-HOC6H3 2a, Ph 4m, 64
14 1e, 3,5-(MeO)2C6H3 2j, 4-NO2C6H4 4n, 76
15 1a, Ph 2k, 2-naphthyl 4o, 70
16 1a, Ph 2l, 2-FC6H4 4p, 67
17 1a, Ph 2m, 2-furyl 4q, 60c
18 1a, Ph 2n, 2-thienyl 4r, 62
19 1a, Ph 2o, 1-naphthyl 4s, 75
20 1f, 4-FC6H4 2h, 3,4-(MeO)2C6H3 4t, 73
21 1g, 4-ClC6H4 2h, 3,4-(MeO)2C6H3 4u, 72
22 1h, 4-BrC6H4 2h, 3,4-(MeO)2C6H3 4v, 66
23 1i, 4-MeC6H4 2h, 3,4-(MeO)2C6H3 4w, 74
24 1c, 3-MeOC6H4 2h, 3,4-(MeO)2C6H3 4x, 64
25 1j, 3-MeO-2-HOC6H3 2a, Ph 4y, 60
26 1k, 2-NO2C6H4 2a, Ph 4z, —d
a

All reactions were run on a 1.0 mmol scale with phenols 1a–1k, cinnamoyl chlorides (2a–2o, 1.0 equiv.), BiCl3 (315 mg, 1.0 equiv.), CCl4 (20 mL), 10 h, reflux (77 °C); then RuCl3·3H2O (261 mg, 1.0 equiv.) was added into the reaction mixture, 5 h, reflux (monitored by TLC).

b

Isolated yields.

c

3q (10%) was obtained.

d

No detection.