Communications
Table 2: Conjugated compounds obtained by Pd-catalyzed coupling with halides.
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Entry
1
Phenol
Electrophile
Coupling product
Yield [%][a]
99
1a
4
5
2
3
1a
87
1a
1e
6
7
82[b]
4
1a[c]
74
5
6
1a
1e
8
9
89
67
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7
8
1a
1a
10
11
94
92
9
1d
12
13
88
93
10
1g
1g
11
12
14
15
91
48
1a
1g
[a] Yield of the isolated products. [b] Symmetric coupling products were obtained in about 15% yield
(GC analysis). [c] 10 mol% of palladium and 40 mol% of P(tBu)3 were used. [d] E/Z=43:57, as
determined by H NMR spectroscopic analysis.
1
[9] Diethylzinc is too weak as a base to deprot-
onate the amine.
[10] A. Erxleben, Inorg. Chem. 2001, 40, 208 –
213.
Keywords: benzoheterole · conjugation · cyclization ·
heterocycles · palladium · zinc
.
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Angew. Chem. Int. Ed. 2006, 45, 944 –947