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. 2022 Feb 1;13(8):2418–2422. doi: 10.1039/d1sc06234d

Optimization studiesa.

graphic file with name d1sc06234d-u1.jpg
Entry Catalyst Solvent Temp. (°C) 8 yield (%)
1 10 THF 80 67
2 11 THF 80 53
3 FeCl3 DCE rt 0
4 FeCl3 DCE 80 0
5 TFA THF 80 0b
6 10 i-PrOH 80 31
7 10 CH3CN 80 28
8 10 EtOAc 80 26
9 10 Toluene 80 24
10 10 THF 90 87
11 10 THF 100 96c
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a

Conditions: substrate 8 (0.2 mmol) and 5 mol% catalyst in 0.4 mL of solvent (0.5 M) in a 5 mL sealed tube were heated to the temperature indicated for 15 h. Yields were determined by 1H NMR using CH2Br2 as an internal standard.

b

2 equiv. of TFA was used.

c

85% isolated yield.