One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids. Issue 6 (9th February 2017)

• Record Type: Journal Article
• Authors: Shen, Xu; Liu, Ping; Liu, Yang; Liu, Yan; Dai, Bin
• Is Part Of: Tetrahedron. Volume 73:Issue 6(2017)
• Page Start: 785
• Page End: 793
• Publication Date: 2017-02-09
• Subjects: Acetyl naphthalene -- Metal-free -- Reductive coupling -- N-tosylhydrazones -- Arylboronic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.12.068
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: