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A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers

A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers
A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers
The paper describes a new method of synthesizing biaryls and triaryls through an intramolecular ipso-substitution reaction initiated by the addition of an aryl radical to a benzyl ether. A tandem variant of the reaction has also been demonstrated. A short synthesis of isoaucuparin 27, a natural product found in the sapwood tissue of Sorbus aucuparia, is also described.
radicals and radical reactions, natural products, aromatic chemistry, cascade reactionscondensed thiophenes
0040-4039
961-964
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Newman, N. A.
d8631f73-4cbd-46ad-b2ea-da254ff8a79f
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Newman, N. A.
d8631f73-4cbd-46ad-b2ea-da254ff8a79f
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59

Harrowven, D. C., Nunn, M. I. T., Newman, N. A. and Fenwick, D. R. (2001) A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers. Tetrahedron Letters, 42 (5), 961-964. (doi:10.1016/S0040-4039(00)02111-0).

Record type: Article

Abstract

The paper describes a new method of synthesizing biaryls and triaryls through an intramolecular ipso-substitution reaction initiated by the addition of an aryl radical to a benzyl ether. A tandem variant of the reaction has also been demonstrated. A short synthesis of isoaucuparin 27, a natural product found in the sapwood tissue of Sorbus aucuparia, is also described.

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More information

Published date: 29 January 2001
Keywords: radicals and radical reactions, natural products, aromatic chemistry, cascade reactionscondensed thiophenes

Identifiers

Local EPrints ID: 19507
URI: http://eprints.soton.ac.uk/id/eprint/19507
ISSN: 0040-4039
PURE UUID: 6e0f9cfd-8f1f-4fd6-a2c3-d70be7ebdabc
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 12 Nov 2019 02:01

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