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. Author manuscript; available in PMC: 2013 Jan 6.
Published in final edited form as: Org Lett. 2011 Dec 8;14(1):94–97. doi: 10.1021/ol202883v

Table 1.

Optimization of iminium ion formation

graphic file with name nihms343236t1.jpg
entry conditions yielda
1 Ir (1 mol %), EtO2CCH2Br (3 equiv), DMF, white Light, NaCN (5 equiv) 36
2 Ru (1 mol %), (EtO2C)2CHBr (3 equiv), DMF, blue LEDs, NaCN (5 equiv) 95
3 Ru (1 mol %), CCl4DMF (1:1), blue LEDs, NaCN (5 equiv) 36
4 Ru (1 mol %), CCl4 (3 equiv), CH3CN, blue LEDs, NaCN (5 equiv) 53
5 Ru (1 mol %), BrCCl3 (3 equiv), DMF, blue LEDs, NaCN (5 equiv) 60
6 Ru (1 mol %), BrCCl3 (3 equiv), DMF, blue LEDs then no light, NaCN (5 equiv) 85
7 Ru (1 mol %), BrCCl3 (3 equiv), DMF, blue LEDs then no light, Bu4NCN (5 equiv) 17
8 Ru (1 mol %), BrCCl3 (3 equiv), THF, blue LEDs then no light, NaCN (5 equiv) NR
9 Ru (1 mol %), BrCCl3 (3 equiv), THF:H2O (2:1), blue LEDs then no light, NaCN (5 equiv) 83
a

Isolated percent yields after chromatography on SiO2.