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. Author manuscript; available in PMC: 2010 Sep 16.
Published in final edited form as: J Am Chem Soc. 2009 Sep 16;131(36):12898–12899. doi: 10.1021/ja905768k

Table 1.

Pd-catalyzed formation of 4-nitro-n-butylbenzene.

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Entry L 5% PTC Yielda Entry L 5% PTC Yielda
1 1 -- 26% 6 3 TDA 10%
2 1 TDA 52% 7 4 TDA 0%
3 1 TBACl 3% 8 5 TDA 0%
4 1 15-C-5 33% 9 1 -- 2%b
5 2 TDA 0% 10 1 TDA 99%c
a

4-chloro-n-butylbenzene (1 mmol), NaNO2 (2.0 mmol), Pd2(dba)3 (0.5 mol%), ligand (1.2 mol%), t-BuOH (2 mL), 110 °C, 24 h; GC yields.

b

(TBA)NO2 was used.

c

Reaction temperature was 130 °C.