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. 2020 Jul 13;5(29):18515–18526. doi: 10.1021/acsomega.0c02590

Table 2. Effect of PTAs on the Aqueous-Phase Reaction of 1a and 2aa.

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entry PTA amount of PTA yield (%)
1 TBAI 20 mol % 67
2 TBAI 1.0 equiv 75
3 TBAI 2.0 equiv 85
4 TBAI 3.0 equiv 88
5 TBAB 2.0 equiv 74
6 TBAC 2.0 equiv 68
7 TBAC/KI 2.0 equiv 83
8 SDS 2.0 equiv 79
9 PEG 2000 10 mol % 82
10 Tween 80 10 mol % 66
11b TBAI 2.0 equiv 76
12c TBAI 2.0 equiv 80
a

Reaction conditions: 1a (0.3 mmol), 2a (0.6 mmol), H2O (3 mL) 100 °C (oil bath), 24 h, under air. TBAI: tetrabutylammonium iodide, TBAB: tetrabutylammonium bromide, TBAC: tetrabutylammonium chloride, SDS: sodium dodecane-1-sulfonate.

b

80 °C.

c

Under Ar.