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

Stuart Aiken; Ben Armitage; Christopher D. Gabbutt; Bernard Heron

doi:10.1016/j.tetlet.2015.06.081

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

Stuart Aiken, Ben Armitage, Christopher D. Gabbutt, Bernard Heron

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8 Citations (Scopus)

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 language	English
Pages (from-to)	4840-4842
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	33
Early online date	10 Jul 2015
DOIs	https://doi.org/10.1016/j.tetlet.2015.06.081
Publication status	Published - 12 Aug 2015

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@article{9faa750fb7d74a99b21f16bf498b9921,

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. {\textcopyright} 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 = aug,

day = "12",

doi = "10.1016/j.tetlet.2015.06.081",

language = "English",

volume = "56",

pages = "4840--4842",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "33",

}

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

UR - http://www.scopus.com/inward/record.url?scp=84936985602&partnerID=8YFLogxK

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 -

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

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Christopher Gabbutt

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

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Christopher Gabbutt

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