Table 2.
Library Data for Compounds 8{1–20} and 9{1–24}
| alkyne 7/8 | R1 | R2 | t (h) | yield (%)b | 3-iodobenzofurana9 | yield (%)b |
|---|---|---|---|---|---|---|
| 7{1} | 4-MeOC6H4 | - | - | - | 9{1} | 97 |
| 7{2} | 3-MeC6H4 | - | - | - | 9{2} | 92 |
| 7{3} | 4-MeOC6H4 | - | - | - | 9{3} | 76 |
| 7{4} | 3,5-(MeO)2C6H3 | - | - | - | 9{4} | 58 |
| 8{1} | 4-MeOC6H4 | 10{1} | 8 | 69 | 9{5} | 93 |
| 8{2} | 4-MeOC6H4 | 10{4} | 8 | 63 | 9{6} | 89 |
| 8{3} | 4-MeOC6H4 | 10{6} | 8 | 57 | 9{7} | 87 |
| 8{4} | 4-MeOC6H4 | 10{7} | 8 | 63 | 9{8} | 90 |
| 8{5} | 4-MeOC6H4 | 10{8} | 8 | 72 | 9{9} | 83 |
| 8{6} | 3-thiophenyl | 10{1} | 8 | 78 | 9{10} | 91 |
| 8{7} | 3-thiophenyl | 10{4} | 8 | 81 | 9 {11} | 83 |
| 8{8} | 3-thiophenyl | 10{6} | 8 | 62 | 9{12} | 78 |
| 8{9} | 3-thiophenyl | 10{7} | 8 | 83 | 9{13} | 88 |
| 8{10} | 1-cyclohexenyl | 10{4} | 8 | 71 | 9{14} | 91 |
| 8{11} | 1-cyclohexenyl | 10{6} | 8 | 68 | 9{15} | 88 |
| 8{12} | 1-cyclohexenyl | 10{7} | 8 | 68 | 9{16} | 92 |
| 8{13} | 3-MeC6H4 | 10{4} | 8 | 67 | 9{17} | 87 |
| 8{14} | 4-MeOC6H4 | 10{1} | 24 | 38(14)c | 9{18} | 82 |
| 8{15} | 4-MeOC6H4 | 11{1} | 12 | 78 | 9{19} | 84 |
| 8{16} | 3-MeC6H4 | 11{1} | 12 | 73 | 9{20} | 82 |
| 8{17} | 3-thiophenyl | 11{1} | 12 | 71 | 9{21} | 81 |
| 8{18} | 3-MeC6H4 | 11{2} | 12 | 59 | 9{22} | 77 |
| 8{19} | 4-MeOC6H4 | 11{3} | 3 | 87 | 9{23} | 51d |
| 8{20} | 4-MeOC6H4 | 11{4} | 3 | 93 | 9{24} | 28d,e |
a
All reactions were carried out using alkynes 7{1–4} or 8{1–20} and 1.5 equiv of IC1 in CH2C12 at room temperature within 2–3 h, unless otherwise indicated.
b
Isolated yields after column chromatography.
c
Some starting material remained. In parentheses is the yield of the Suzuki-Miyaura direct coupling product.
d
IC1 (2.0 + 1.0 equiv) was used.
e
An inseparable mixture was obtained.