An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols

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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. © 2015 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)4840-4842
JournalTetrahedron Letters
Volume56
Issue number33
DOIs
Publication statusPublished - 12 Aug 2015

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title = "An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols",
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. {\circledC} 2015 Elsevier Ltd. All rights reserved.",
keywords = "4-Aryl-2-naphthol, But-2-yn-1-ols, Intramolecular α-arylation, Meyer-Schuster rearrangement, Naphthopyran, Photochromism",
author = "Stuart Aiken and Ben Armitage and Gabbutt, {Christopher D.} and Bernard Heron",
year = "2015",
month = "8",
day = "12",
doi = "10.1016/j.tetlet.2015.06.081",
language = "English",
volume = "56",
pages = "4840--4842",
journal = "Tetrahedron Letters",
issn = "0040-4039",
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}

An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols. / Aiken, Stuart; Armitage, Ben; Gabbutt, Christopher D.; Heron, Bernard.

In: Tetrahedron Letters, Vol. 56, No. 33, 12.08.2015, p. 4840-4842.

Research output: Contribution to journalArticle

TY - JOUR

T1 - An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols

AU - Aiken, Stuart

AU - Armitage, Ben

AU - Gabbutt, Christopher D.

AU - Heron, Bernard

PY - 2015/8/12

Y1 - 2015/8/12

N2 - 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. © 2015 Elsevier Ltd. All rights reserved.

AB - 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. © 2015 Elsevier Ltd. All rights reserved.

KW - 4-Aryl-2-naphthol

KW - But-2-yn-1-ols

KW - Intramolecular α-arylation

KW - Meyer-Schuster rearrangement

KW - Naphthopyran

KW - Photochromism

U2 - 10.1016/j.tetlet.2015.06.081

DO - 10.1016/j.tetlet.2015.06.081

M3 - Article

VL - 56

SP - 4840

EP - 4842

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 33

ER -