Iron-catalyzed oxidative cross-coupling of phenols and alkenes

Umesh A. Kshirsagar; Clil Regev; Regev Parnes; Doron Pappo

doi:10.1021/ol401532a

Iron-catalyzed oxidative cross-coupling of phenols and alkenes

Umesh A. Kshirsagar, Clil Regev, Regev Parnes, Doron Pappo

Department of Chemistry

Ben-Gurion University of the Negev

Research output: Contribution to journal › Article › peer-review

Abstract

A novel bioinspired iron-catalyzed oxidative cross-coupling reaction between phenols and conjugated alkenes was developed. This method enables the direct coupling of phenols with styrene, α-alkyl- and α- arylstyrenes, β-alkyl styrenes, and stilbenes, thereby providing a new strategy for the preparation of the pharmacologically important 2,3-dihydrobenzofuran motif. In addition, this study revealed that under a different set of conditions an oxidative/addition dearomatization reaction of 1,1′-bi-2-naphthol (BINOL) with styrene can take place.

Original language	American English
Pages (from-to)	3174-3177
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	12
DOIs	https://doi.org/10.1021/ol401532a
State	Published - 21 Jun 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol401532a

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title = "Iron-catalyzed oxidative cross-coupling of phenols and alkenes",

abstract = "A novel bioinspired iron-catalyzed oxidative cross-coupling reaction between phenols and conjugated alkenes was developed. This method enables the direct coupling of phenols with styrene, α-alkyl- and α- arylstyrenes, β-alkyl styrenes, and stilbenes, thereby providing a new strategy for the preparation of the pharmacologically important 2,3-dihydrobenzofuran motif. In addition, this study revealed that under a different set of conditions an oxidative/addition dearomatization reaction of 1,1′-bi-2-naphthol (BINOL) with styrene can take place.",

author = "Kshirsagar, \{Umesh A.\} and Clil Regev and Regev Parnes and Doron Pappo",

year = "2013",

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doi = "10.1021/ol401532a",

language = "American English",

volume = "15",

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journal = "Organic Letters",

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T1 - Iron-catalyzed oxidative cross-coupling of phenols and alkenes

AU - Kshirsagar, Umesh A.

AU - Regev, Clil

AU - Parnes, Regev

AU - Pappo, Doron

PY - 2013/6/21

Y1 - 2013/6/21

N2 - A novel bioinspired iron-catalyzed oxidative cross-coupling reaction between phenols and conjugated alkenes was developed. This method enables the direct coupling of phenols with styrene, α-alkyl- and α- arylstyrenes, β-alkyl styrenes, and stilbenes, thereby providing a new strategy for the preparation of the pharmacologically important 2,3-dihydrobenzofuran motif. In addition, this study revealed that under a different set of conditions an oxidative/addition dearomatization reaction of 1,1′-bi-2-naphthol (BINOL) with styrene can take place.

AB - A novel bioinspired iron-catalyzed oxidative cross-coupling reaction between phenols and conjugated alkenes was developed. This method enables the direct coupling of phenols with styrene, α-alkyl- and α- arylstyrenes, β-alkyl styrenes, and stilbenes, thereby providing a new strategy for the preparation of the pharmacologically important 2,3-dihydrobenzofuran motif. In addition, this study revealed that under a different set of conditions an oxidative/addition dearomatization reaction of 1,1′-bi-2-naphthol (BINOL) with styrene can take place.

UR - http://www.scopus.com/inward/record.url?scp=84879395307&partnerID=8YFLogxK

U2 - 10.1021/ol401532a

DO - 10.1021/ol401532a

M3 - Article

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VL - 15

SP - 3174

EP - 3177

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Iron-catalyzed oxidative cross-coupling of phenols and alkenes

Abstract

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