An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols. Issue 33 (12th August 2015)

• Record Type: Journal Article
• Authors: Aiken, Stuart; Armitage, Ben; Gabbutt, Christopher D.; Heron, B. Mark
• Is Part Of: Tetrahedron letters. Volume 56:Issue 33(2015)
• Page Start: 4840
• Page End: 4842
• Publication Date: 2015-08-12
• Subjects: But-2-yn-1-ols -- Meyer–Schuster rearrangement -- Intramolecular α-arylation -- 4-Aryl-2-naphthol -- Naphthopyran -- Photochromism; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.081
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 1-Aryl-1-(2-bromophenyl)but-2-yn-1-ols, obtained from the addition of prop-1-yn-1-yllithium to 2-bromobenzophenones, readily rearrange to 4-aryl-4-(2-bromophenyl)but-3-en-2-ones upon treatment with TFA. Subsequent intramolecular Pd-mediated α-arylation of these but-3-en-2-ones gave 4-aryl-2-naphthols which were smoothly transformed into photochromic naphthopyrans.