One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids

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• 作者：Xu Shen ; Ping Liu ; ^{liuping1979112@aliyun.com} ; Yang Liu ; Yan Liu ; ^{liuyan1979810@aliyun.com} ; Bin Dai
• 关键词：Acetyl naphthalene ; Metal-free ; Reductive coupling ; N-tosylhydrazones ; Arylboronic acid
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：9 February 2017
• 年：2017
• 卷：73
• 期：6
• 页码：785-793
• 全文大小：992 K
• 卷排序：73

文摘

In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.