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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 2.

ATRA Using Photoredox Catalysisa

entry substrate olefin product yieldb
graphic file with name nihms-278782-t0003.jpg graphic file with name nihms-278782-t0004.jpg
1 4 R = CH2NHTs 67c
2 4 R = CH2NHBoc 99
3 4 R = (CH2)4OH 95
4 4 R = (CH2)3OH 99
5 4 R = (CH2)4OTBS 90
6 4 R = (CH2)4OCH2Ph 92
7 4 R = (CH2)3Br 92
8 4 R = (CH2)4CO2Et 99
9 4 graphic file with name nihms-278782-t0005.jpg graphic file with name nihms-278782-t0006.jpg 95d
10 CF3I graphic file with name nihms-278782-t0007.jpg graphic file with name nihms-278782-t0008.jpg 90e,f
11 CF3I graphic file with name nihms-278782-t0009.jpg graphic file with name nihms-278782-t0010.jpg 81e,f
12 graphic file with name nihms-278782-t0011.jpg graphic file with name nihms-278782-t0012.jpg graphic file with name nihms-278782-t0013.jpg 93
13 graphic file with name nihms-278782-t0014.jpg graphic file with name nihms-278782-t0015.jpg graphic file with name nihms-278782-t0016.jpg 75
14 CCl3Br graphic file with name nihms-278782-t0017.jpg graphic file with name nihms-278782-t0018.jpg 87f
15 graphic file with name nihms-278782-t0019.jpg graphic file with name nihms-278782-t0020.jpg graphic file with name nihms-278782-t0021.jpg 99d
16 graphic file with name nihms-278782-t0022.jpg graphic file with name nihms-278782-t0023.jpg graphic file with name nihms-278782-t0024.jpg 84d
a

Reaction conditions: 1 (1.0 mol %), haloalkane (2.0 equiv), and LiBr (2.0 equiv) in DMF/H2O (1:4).

b

Isolated yield (%) after purification on SiO2.

c

90% brsm.

d

dr 1:1.

e

Excess of haloalkane was used.

f

No LiBr added.