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J ¼ 16.0, 1 H); 7.95 (d, J ¼ 8.5, 2 H). 13C-NMR: 26.6; 28.1; 80.9; 122.7; 127.9; 128.7; 137.7; 139.0; 141.9;
165.7; 197.3.
1-(4-Methylstyryl)benzene ( ¼ 1-Methyl-4-[(E)-2-phenylethenyl]benzene) [11]. 1H-NMR: 2.36 (s,
3 H); 7.07 (s, 2 H); 7.17 (d, J ¼ 8.0, 2 H); 7.24 – 7.26 (m, 1 H); 7.35 (d, J ¼ 7.5, 2 H); 7.41 (d, J ¼ 8.1, 2 H);
7.51 (d, J ¼ 7.9, 2 H). 13C-NMR: 21.2; 126.3; 126.4; 127.4; 127.7; 128.6; 128.6; 129.3; 134.5; 137.4; 137.5.
tert-Butyl (E)-3-(4-Methylphenyl)acrylate (¼ tert-Butyl (2E)-3-(4-Methylphenyl)prop-2-enoate)
1
[13]. H-NMR: 1.54 (s, 9 H); 2.35 (s, 3 H); 6.33 (d, J ¼ 16.0, 1 H); 7.16 (d, J ¼ 8.0, 2 H); 7.39 (d, J ¼ 8.0,
2 H); 7.58 (d, J ¼ 16.0, 1 H). 13C-NMR: 21.3; 28.1; 80.1; 118.9; 129.4; 131.8; 137.8; 140.1; 143.4; 166.4.
1-(4-Methoxystyryl)benzene ( ¼ 1-Methoxy-4-[(E)-2-phenylethenyl]benzene) [11]. 1H-NMR: 3.83 (s,
3 H); 6.89 (d, J ¼ 8.8, 2 H); 6.98 (d, J ¼ 16.5, 1 H); 7.08 (d, J ¼ 16.4, 1 H); 7.25 (t, J ¼ 7.0, 1 H); 7.34 (t, J ¼
7.5, 2 H); 7.44 – 7.50 (m, 4 H). 13C-NMR: 55.3; 114.1; 126.3; 126.6; 127.2; 127.7; 128.2; 128.6; 130.2; 137.7;
159.3.
tert-Butyl (E)-3-(4-Cyanophenyl)acrylate ( ¼ tert-Butyl (2E)-3-(4-Cyanophenyl)prop-2-enoate)
1
[13]. H-NMR: 1.53 (s, 9 H); 6.44 (d, J ¼ 16.0, 1 H); 7.56 (d, J ¼ 15.8, 1 H); 7.58 (d, J ¼ 8.2, 2 H); 7.65
(d, J ¼ 8.2, 2 H). 13C-NMR: 28.1; 81.2; 113.0; 128.8; 131.6; 132.5; 139.0; 141.0; 165.3.
MizorokiꢀHeck Arylation in Aqueous Media Catalyzed by Pincers 1 or 2. General Procedure. A dry
10-ml screw-capped tube was charged with the aryl bromide (1 mmol), alkene (1.5 mmol), K2CO3
(2 mmol), catalyst 1 or 2 (1 mmol Pd), TBAF (1 mmol), and dist. H2O (2 ml). The mixture was stirred at
1308 for 22 h. After cooling, H2O (5 ml) was added, and the aq. layer was extracted with AcOEt (4 ꢂ
6 ml). The combined org. extracts were dried (Na2SO4) and evaporated in vacuo. The residue was
1
dissolved in CDCl3 and analyzed by H-NMR (with bis(ethylene glycol) dimethyl ether as an internal
standard), thus confirming the identity of every product in comparison with the spectroscopic data in the
literature.
1-(4-Styrylphenyl)ethanone (¼1-{4-[(E)-2-Phenylethenyl]phenyl}ethanone) [11].
tert-Butyl (E)-3-(4-Methylphenyl)acrylate (¼tert-Butyl (2E)-3-(4-Methylphenyl)prop-2-enoate)
[13].
1-(4-Nitrostyryl)benzene (¼1-Nitro-4-[(E)-2-phenylethenyl]benzene) [12]. 1H-NMR: 7.14 (d, J ¼
16.0, 1 H); 7.27 (d, J ¼ 16.0, 1 H); 7.33 – 742 (m, 3 H); 7.55 (d, J ¼ 7.8, 2 H); 7.63 (d, J ¼ 8.8, 2 H); 8.22
(d, J ¼ 8.8, 2 H). 13C-NMR: 124.2; 126.4; 127.0; 127.1; 129.0; 129.0; 129.0; 133.4; 136.3; 144.0; 146.9.
tert-Butyl (E)-3-(4-Nitrophenyl)acrylate (¼tert-Butyl (2E)-3-(4-Nitrophenyl)prop-2-enoate) [12].
1H-NMR: 1.55 (s, 9 H); 6.50 (d, J ¼ 15.9, 1 H); 7.61 (d, J ¼ 15.9, 1 H); 7.65 (d, J ¼ 7.8, 2 H); 8.24 (d, J ¼ 8.7,
2 H). 13C-NMR: 28.9; 82.0; 124.8; 125.3; 129.2; 141.2; 141.6; 149.0; 165.9.
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