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. 2017 Mar 24;8(5):4044–4050. doi: 10.1039/c6sc05697k

Table 1. Studies of the promotion effect of amides, their derivatives, amines and amine alcohols in the Cα-heteroarylation of tetrahydrofuran with isoquinoline and the optimization of the reaction conditions a .

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Entry Oxidant Additive 1a (equiv.) Yield b
1 (NH4)2S2O8 20 14%
2 (NH4)2S2O8 A1 20 77%
3 (NH4)2S2O8 A2 20 15%
4 (NH4)2S2O8 A3 20 24%
5 (NH4)2S2O8 A4 20 50%
6 (NH4)2S2O8 A5 20 53%
7 (NH4)2S2O8 A6 20 55%
8 (NH4)2S2O8 A7 20 70%
9 (NH4)2S2O8 A8 20 7%
10 (NH4)2S2O8 A9 20 15%
11 (NH4)2S2O8 A10 20 80%
12 (NH4)2S2O8 A11 20 82%
13 (NH4)2S2O8 A12 20 5%
14 (NH4)2S2O8 A13 20 88%
15 (NH4)2S2O8 A13 20 42% c
16 (NH4)2S2O8 A13 20 82% d
17 (NH4)2S2O8 A13 20 75% e
18 (NH4)2S2O8 A13 10 82%
19 (NH4)2S2O8 A13 10 80% f
20 (NH4)2S2O8 A13 5 60% f
21 (NH4)2S2O8 A13 5 67% f , g

aConditions employed 1a (2.5–10.0 mmol), 2a (0.5 mmol), oxidant (1.5 mmol), additive (1.0 mmol), 40 °C, 24 h, and a solvent mixture (1.5 mL, MeCN : H2O = 1 : 1), unless otherwise noted.

bThe yields were determined using 1H NMR with CH2Br2 as an internal standard.

cPerformed with (NH4)2S2O8 (1 equiv.).

dPerformed with A13 (1 equiv.).

ePerformed with A13 (0.5 equiv.).

fWater (1.5 mL) was used as the solvent.

gPerformed on a 1 g scale.