Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

Tomoya Miura; Hiroshi Shimizu; Tomohiro Igarashi; Masahiro Murakami

doi:10.1039/c0ob00163e

Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

Tomoya Miura, Hiroshi Shimizu, Tomohiro Igarashi, Masahiro Murakami

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

19 Citations (Scopus)

Abstract

Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent δ-elimination of Rh(i)-OH.

Original language	English
Pages (from-to)	4074-4076
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	18
DOIs	https://doi.org/10.1039/c0ob00163e
Publication status	Published - Sep 21 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent δ-elimination of Rh(i)-OH.",

author = "Tomoya Miura and Hiroshi Shimizu and Tomohiro Igarashi and Masahiro Murakami",

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AU - Miura, Tomoya

AU - Shimizu, Hiroshi

AU - Igarashi, Tomohiro

AU - Murakami, Masahiro

PY - 2010/9/21

Y1 - 2010/9/21

N2 - Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent δ-elimination of Rh(i)-OH.

AB - Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent δ-elimination of Rh(i)-OH.

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JO - Organic and Biomolecular Chemistry

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ER -

Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

Abstract

ASJC Scopus subject areas

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