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. 2018 May 25;9(24):5389–5393. doi: 10.1039/c8sc00999f

Table 1. Summary of optimization studies.

Inline graphic
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 at 65 °C 21/0 18 0
5 at 65 °C, n-BuOH 8/0 36 0
6 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.