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. 2013 Jun 21;6(8):1455–1460. doi: 10.1002/cssc.201300239

Table 4.

Amination of 2-halopyridines.[a]Inline graphic

Entry Amine Product (yield [%]) for the reaction with
Inline graphic Inline graphic Inline graphic Inline graphic
1 Inline graphic (<5) (6) 37 (60) 43 (96)
2 Inline graphic (<5) no reaction 38 (65) 44 (70)
3 Inline graphic (<5) no reaction 39 (48; MW 59)[b] 45 (73)
4 Inline graphic 34 (<5) 34 (54) 40 (53) 46 (74)
5 Inline graphic 35 (9; MW 25)[b] 35 (16) 41 (36) 47 (87)
6 Inline graphic 36 (21)[c] 36 (46)[c] 42 (85) 48 (76)
7 Inline graphic no reaction no reaction no reaction 49 (73)
[a]

All reactions were performed with aryl halide (1 equiv.), amine (1 equiv.) and KF (2 equiv.) in water at 100 °C for 17 h.

[b]

MW refers to the yield if the reaction was performed in a microwave reactor (300 W) at 175 °C for 1 h (2 h in the case of furfurylamine) with KF (1 equiv.).

[c]

Yield reported as an NMR yield calculated from the internal standard using 1,4-dioxane.