Table 1. Summary of optimization studies.
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Entry | Modification a , b , c | Time d (h) | 3 e (%) | Recovered 4 e (%) |
1 | None | 12/6 | 51 | 26 |
2 | n-BuOH | 12/2 | 67 | 9 |
3 | n-BuOH, no Et3N | 12/2 | 50 f | 14 |
4 | hν at 65 °C | 21/0 | 18 | 0 |
5 | hν at 65 °C, n-BuOH | 8/0 | 36 | 0 |
6 | hν at 65 °C with Et3N | 24/0 | 24 | 0 |
7 | None, gram-scale | 55/6 | 61 | 24 |
8 | n-BuOH, gram-scale | 34/2 | 59 | 22 |
aPhotochemistry was carried out using 24 W UV-lamps.
bReactions performed in a 50 mL quartz flask on 0.5 mmol scale, unless otherwise noted.
cGram-scale reactions were carried out a 100 mL quartz flask.
dReaction times are reported as follows: time exposed to UV-light/time of conventional heating on the bench-top (see the ESI for a detailed description of reaction step).
eIsolated yield after purification.
fSide product 11 was formed in 10–15% yield.