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. 2021 Oct 1;1(11):2080–2087. doi: 10.1021/jacsau.1c00360

Table 2. Substrate Scope for Cyclotrimerizationa.

graphic file with name au1c00360_0008.jpg

entry substrate 1 (Ar) yield of 2 (%)
1 Ph, 1a 68
2 4-MeC6H4, 1b 84
3 3-MeC6H4, 1c 77
4 2-MeC6H4, 1d 67
5 4-MeOC6H4, 1e 86
6 4-BuC6H4, 1f 79
7 4-BrC6H4, 1g 66b
8 4-ClC6H4, 1h 61b
9 4-FC6H4, 1i 53
10 4-CF3C6H4, 1j 42
11 4-EtO2CC6H4, 1k 46
12 4-MeCOC6H4, 1l 39b
13 4-HOC6H4, 1m 71b
14 4-PhC6H4, 1n 49b
15 2-PhC6H4, 1o 42b
16 3-Py, 1p 0b
17 1-naphthyl, 1q 41
18 1-octyne (1r) 0
19 (triisopropylsilyl)acetylene (1s) 0
20 1,2-diphenylethyne (1t) 0b
a

Reaction conditions: 1 (1 mol equiv., 5 mmol), P4VP-CoCl2 (0.033 mol %, 330 mol ppm of Co), DIPEA (6.5 mol %), 150 °C, 24 h, N2 atmosphere. Isolated yield.

b

One-half a milliliter of xylene was added.