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. Author manuscript; available in PMC: 2012 Mar 30.
Published in final edited form as: J Am Chem Soc. 2011 Mar 7;133(12):4160–4163. doi: 10.1021/ja108560e

Table 1.

Optimization of Reaction Conditions/Control Experiments

graphic file with name nihms-278782-t0002.jpg

entry R conditionsa yieldb
1 CH2NHTs (2a) 4 (2.0 equiv), DMF 17
2 2a 4 (2.0 equiv), LiBF4 (2.0 equiv), DMF 25
3 2a 4 (2.0 equiv), LiBr (2.0 equiv), DMF 45
4 2a 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (4:1) 54
5 2a 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (1:4) 67
6 CH2NHBoc (2b) 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (1:4) 99
7 (CH2)4OH (2c) 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (1:4) 99
8 2c 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (1:4), , no light 0
9 2c no catalyst, 4 (2.0 equiv), LiBr (2.0 equiv), DMF/H2O (1:4) 0
10 2c 4 (1.1 equiv), LiBr (1.1 equiv), DMF/H2O (1:4) 97
11 2c 4 (0.95 equiv), LiBr (0.95 equiv), DMF/H2O (1:4) 95
12 2c 4 (2.0 equiv), no additive, DMF/H2O (1:4) 72
13 2c 4 (2.0 equiv), LiBr (2.0 equiv), DMF 46
a

Entries 1–6 were degassed (freeze-pump-thaw).

b

Isolated yield (%) after purification on SiO2.