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. Author manuscript; available in PMC: 2012 Sep 12.
Published in final edited form as: ACS Comb Sci. 2011 Jul 13;13(5):501–510. doi: 10.1021/co200090p

Table 1.

Sequential Preparation of Alkynes 2{1–15} and 3{1–11} from Aryl Halides 1

graphic file with name nihms309970u2.jpg
entry R1 R2 R3 X alkyne 2 yield (%)a alkyne 3 yield (%)a
1 H H H SMe 2{1} 88
2 H H 4-MeO SMe 2{2} 88
3 H H 3-MeO SMe 2{3} 77
4 H H 2-MeO SMe 2{4} 79
5 MeO H 4-MeO Br 2{5} 94 3{1} 86
6 MeO H 3-MeO Br 2{6} 91 3{2} 93
7 MeO H 2-MeO Br 2{7} 87 3{3} 89
8 MeO H 3,5-(MeO)2 Br 2{8} 83 3{4} 83
9 H MeO 4-MeO Br 2{9} 73 3{5} 81
10 H MeO 2-MeO Br 2{10} 77 3{6} 90
11 MeO MeO 4-MeO Br 2{11} 92 3{7} 87
12 MeO MeO 3-MeO Br 2{12} 79 3{8} 63
13 MeO MeO 2-MeO Br 2{13} 71 3{9} 91
14 OCH2O 4-MeO Br 2{14} 84b 3{10} 73
15 OCH2O 2-MeO Br 2{15} 83b 3{11} 63
a

Isolated yields after column chromatography.