Bisarylation of 1,1′,3,3′-Tetrahalo-2,2′-biazulene under Suzuki–Miyaura Cross-coupling Conditions
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1,3-Bisarylated-2,2′-biazulene <b>1</b> and 1,1′-bisarylated-2,2′-biazulene <b>1</b>′ were obtained by the Suzuki–Miyaura cross-coupling reaction of 1,1′,3,3′-tetrahalo-2,2′-biazulene <b>2</b> with 4-<i>tert</i>-butylphenylboronic acid (<b>3b</b>). The other two halogen atoms were reductively removed by hydrogenation under the same reaction conditions. The major regioisomer <b>1</b> was obtained with a selectivity of up to 94% (15:1) and a combined yield of <b>1</b> and <b>1</b>′ of up to 77%.
- Chemistry Letters
Chemistry Letters 43(4), 504-506, 2014
The Chemical Society of Japan