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. Author manuscript; available in PMC: 2014 Apr 1.
Published in final edited form as: Tetrahedron. 2013 Apr;69(13):2701–2713. doi: 10.1016/j.tet.2013.02.003

Table 1.

Optimization of the reaction conditionsa

graphic file with name nihms-445477-t0002.jpg

entry time (min) temp.(°C) solvent ratio 4:5:6 catalyst yield 7b (%)
step 1 step 1 step 1 step 2
1 15 60 Et3N MeCN 1:1.05:1.1 2 mol % PdCl2(PPh3)2 1 mol % CuI 51
2 15 60 Et3N MeCN 1:1.05:1.1 2 mol % Pd(PPh3)4 1 mol % CuI 23
3 15 60 Et3N MeCN 1:1.05:1.1 2 mol % Pd(dppe)2 1 mol % CuI 10
4 15 60 Et3N MeCN 1:1.05:1.1 2 mol % Pd(OAc)2 4 mol % PPh3 1 mol % CuI 6
5 15 60 Et3N MeCN 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 53
6 15 60 iPr2NH MeCN 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 50
7 15 60 Et3N DMF 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 34
8 15 60 Et3N THF 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 29
9 15 60 Et3N Toluene 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 15
10 25 80 Et3N MeCN 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 20
11c 15 25 Et3N MeCN 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 53
12 30 25 Et3N MeCN 1:1.05:1.0 2 mol % PdCl2(PPh3)2 1 mol % CuI 73
13 30 25 Et3N MeCN 1:1.05:1.0 3 mol % PdCl2(PPh3)2 2 mol % CuI 86
14d 30 25 NMM/Et3N MeCN 1:1.2:1.0 3 mol % PdCl2(PPh3)2 2 mol % CuI 89
15e 30 25 THF/Et3N MeCN 1:1.2:1.0 3 mol % PdCl2(PPh3)2 2 mol % CuI 96
a

Unless otherwise noted, all of the reactions were carried out under microwave irradiation on a 1.0 mmol scale in microwave-resistant vials.

b

Isolated yields after column chromatography.

c

When the first step of the reaction was carried out at 25 °C, much cleaner reaction mixtures were obtained than at 60 °C.

d

0.5 mL of N-methylmorpholine (NMM)/1.5 mL of Et3N using anhydrous solvents under argon.

e

0.5 mL of THF/1.0 mL of Et3N, and CuI were added as a solution in 0.5 mL of Et3N using anhydrous solvents under argon.