Table 2 Intermolecular hydroamination of anilines and alkynes catalyzed by [(Z5-Cp*)2Zn2]a
Entry Substrates
5 h, 87%.
(22% bypr)c
18 h, 89% (6% bypr)c
1
2
3
9 h, 95%
9 h, 96%
5 h, Quant.
3.5 h, 82%
15 h, 99%
1 h, 20%
11.25 h, Quant.d 99%b,d
36 h, 93%. (7% bypr)c
4 h, 88%;
10 h, Quant.
18 h, 75% 48 h, 93%
19.66 h, 93%d 21.66 h, 95%d
d
5 h, Quant.
34 h, 99%
25 h, 93%d 48 h, 99%d 19.75 h, 93% 21.75 h, 96%d
e
—
d
4
6.5 h, 82% 30 h, 97%
9 h, 41% 5 h, 38%
9 h, 97%
41.75 h, 69% 43.75 h, 70%d
5 h, 92%
(8% bypr)c
e
—
5
8 h, Quant. (4% bypr)c 3 h, 71%
a
Reagents and conditions: substrate (0.5 mmol), catalyst (2.5 mol%), [PhNMe2H][B(C6F5)4] (2.5 mol%), C6D6, 80 1C, conversion determined by
1H NMR; isolated yield; bypr = byproduct: the corresponding enamine; reaction at room temperature; no conversion.
b
c
d
e
by [(Z5-Cp*)2Zn2] proceeds already at room temperature. Thus,
for this reaction [(Z5-Cp*)2Zn2] is more active than any other
catalyst.
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This journal is The Royal Society of Chemistry 2011