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. 2022 Apr 12;7(16):14357–14362. doi: 10.1021/acsomega.2c01241

Table 1. Optimization of Reaction Conditionsa.

entry SiR3 additive cat. (mol %) light source solvent yieldb (%)
1 TMS DIPEA 1% 10 W blue LED THF 0
2 TMS   1% 10 W blue LED THF trace
3 TES   1% 10 W blue LED THF 13%
4 TIPS   1% 10 W blue LED THF 25%
5 TIPS   1% 10 W blue LED dioxane trace
6 TIPS   1% 10 W blue LED DMF 5%
7 TIPS   1% 10 W blue LED DMSO 5%
8 TIPS   1% 10 W blue LED hexane N.D.
9 TIPS   1% 10 W blue LED CH3CN 50
10 TIPS   1% 5 W blue LED CH3CN 37
11 TIPS   1% 15 W blue LED CH3CN 50
12 TIPS   1% 10 W white LED CH3CN 25
13c TIPS   1% 10 W blue LED CH3CN 69
14c TIPS   2% 10 W blue LED CH3CN 64
15c TIPS   3% 10 W blue LED CH3CN 60
16c,d TIPS   1% 10 W blue LED CH3CN 80
17c,e TIPS   1% 10 W blue LED CH3CN 85
18c,e TIPS     10 W blue LED CH3CN N.D.
19c,e TIPS   1%   CH3CN N.D.
a

Reaction conditions: 1a (0.5 mmol, 1.0 equiv), CF3Br (1.0 atm), photocatalyst (0.005 mmol, 1 mol %) in a 20 mL quartz tube, room temperature, 10 W blue LED.

b

Isolated yield.

c

Replace the air in the container with CF3Br three times and then fill it with CF3Br (1.5 atm).

d

25 mL flask.

e

50 mL Schlenk flask. N.D.: not detected.