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. Author manuscript; available in PMC: 2014 Jan 16.
Published in final edited form as: Org Prep Proced Int. 2013 Jan 16;45(1):66–71. doi: 10.1080/00304948.2013.743755

Table 1.

Yields of 3a–j using Three Catalysts

graphic file with name nihms477976u2.jpg
Product R Yield (%)
Catalyst: (Ph3P)2PdCl2
Pd(OAc)2
Frech
Method: A B A B C D
3a n-C3H7 37 42 50 52 80 80
3b i-C4H9 30 65 67 67 82 81
3c i-C4H7 36 56 65 63 75 76
3d c-C6H11 32 47 54 57 82 82
3e C6H5 26 60 58 55 78 80
3f 4-CH3C6H4 38 67 66 64 76 74
3g 4-FC6H4 28 55 62 63 79 77
3h C6H5CH2 22 56 68 68 83 80
3i 4-CH3C6H4CH2 18 48 56 45 75 71
3j 4-CF3OC6H4CH2 10 25 38 40 74 77

Method A: Round-bottomed flask, 1.30 mmol each of 1 and 2, 1.42 mmol of N-ethylpiperidine, 1.63 × 10−2 mmol of catalyst, 4 mL of DMF, 140°C, 18 h; Method B: Sealed tube, 1.30 mmol of 1 and 2, 1.42 mmol of N-ethylpiperidine, 1.63 × 10−2 mmol of catalyst, 4 mL of DMF, 140°C, 18 h; Method C: Round-bottomed flask, 1.30 mmol of 1 and 2, 1.42 mmol of N-ethylpiperidine, 1.55 × 10−3 mmol of catalyst, 4 mL of DMF, 140°C, 18 h; Method D: Sealed tube, 1.30 mmol of 1 and 2, 1.42 mmol of N-ethylpiperidine, 1.55 × 10−3 mmol of catalyst, 4 mL of DMF, 140°C, 18 h. All reactions were performed under argon.