Skip to main content
. Author manuscript; available in PMC: 2014 Apr 19.
Published in final edited form as: J Org Chem. 2013 Apr 10;78(8):4107–4114. doi: 10.1021/jo400428m

Table 1.

Optimization and control studiesa

graphic file with name nihms463032u2.jpg
entry additive equiv 6 temp time yieldb
1 none 4 23 °C 12 h 60%
2 NaBF4 4 23 °C 12 h 68%
3 NaHCO3 4 23 °C 12 h 70%
4 HCO2H 4 23 °C 12 h 50%
5 CF3CO2H 4 23 °C 12 h 88%
6 TsOH 4 23 °C 12 h 38%
7 CF3CO2H 2 23 °C 12 h 98%
8 CF3CO2H 2 50 °C 5 h 96%
9 none 2 50 °C 5 h 28%
10c CF3CO2H 2 50 °C 5 h 0%
11d CF3CO2H 2 50 °C 5 h 0%
a

Unless otherwise noted, reactions were conducted using 2 mol% Ru(bpy)3Cl2 and 1 equiv of additive in degassed MeCN (0.25 M) and were irradiated using a 23 W compact fluorescent light bulb at a distance of 30 cm.

b

Yields determined by 1H NMR using an internal standard.

c

Reaction conducted in the absence of Ru(bpy)3Cl2.

d

Reaction conducted in the dark.