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. Author manuscript; available in PMC: 2009 Sep 14.
Published in final edited form as: Tetrahedron Lett. 2008 Jun 23;49(26):4147–4148. doi: 10.1016/j.tetlet.2008.04.124

Table 1.

Reduction of Benzylic and Allylic Halides with Pyridine N-Oxide in CH3CN

Entry Substrate Product Temperature Yield
(isolated)
graphic file with name nihms53877t1.jpg graphic file with name nihms53877t2.jpg
1 R = H 25 °C 82%
2 R = p-Br 25 °C 80%
3 R = p-CO2CH3 25 °C 81%
4 R = m-CN 50 °C 84%
5 R = p-CN 50 °C 80%
6 R = m-NO2 50 °C 86%
7 R = p-NO2 50 °C 86%
8 graphic file with name nihms53877t3.jpg graphic file with name nihms53877t4.jpg 25 °C
9 graphic file with name nihms53877t5.jpg graphic file with name nihms53877t6.jpg 25 °C 84%
10 graphic file with name nihms53877t7.jpg graphic file with name nihms53877t8.jpg 25 °C 85%
11 graphic file with name nihms53877t9.jpg graphic file with name nihms53877t10.jpg 25 °C 85%
12 graphic file with name nihms53877t11.jpg graphic file with name nihms53877t12.jpg 50 °C 92%
13 graphic file with name nihms53877t13.jpg graphic file with name nihms53877t14.jpg 50 °C 74%a
14 graphic file with name nihms53877t15.jpg graphic file with name nihms53877t16.jpg 50 °C 75%b
15 graphic file with name nihms53877t17.jpg graphic file with name nihms53877t18.jpg 50 °C 95%
a

The yield is based on 71% converted starting material.

b

The yield is based on 50% converted starting material.