Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters

Gregory R. Ganci; John D. Chisholm

doi:10.1016/j.tetlet.2007.09.137

Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters

Gregory R. Ganci, John D. Chisholm

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31 Scopus citations

Abstract

The metal complex Rh(acac)(CO)₂ in the presence of dicyclohexylphenylphosphine provides a useful catalyst system for the addition of boronic acids to 1,2-diketones and 1,2-ketoesters. The best yields were obtained when the transformation was performed in DME/H₂O at 80 °C with 4 equiv of the boronic acid. The results discussed herein extend the scope of the addition of arylboronic acids to highly activated diketones and ketoesters. The products of the reaction are useful in the synthesis of natural products containing oxygenation next to esters or ketones.

Original language	English (US)
Pages (from-to)	8266-8269
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2007.09.137
State	Published - Nov 19 2007

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.09.137

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title = "Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters",

abstract = "The metal complex Rh(acac)(CO)2 in the presence of dicyclohexylphenylphosphine provides a useful catalyst system for the addition of boronic acids to 1,2-diketones and 1,2-ketoesters. The best yields were obtained when the transformation was performed in DME/H2O at 80 °C with 4 equiv of the boronic acid. The results discussed herein extend the scope of the addition of arylboronic acids to highly activated diketones and ketoesters. The products of the reaction are useful in the synthesis of natural products containing oxygenation next to esters or ketones.",

author = "Ganci, {Gregory R.} and Chisholm, {John D.}",

note = "Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for the support of this research. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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T1 - Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters

AU - Ganci, Gregory R.

AU - Chisholm, John D.

N1 - Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for the support of this research. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2007/11/19

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N2 - The metal complex Rh(acac)(CO)2 in the presence of dicyclohexylphenylphosphine provides a useful catalyst system for the addition of boronic acids to 1,2-diketones and 1,2-ketoesters. The best yields were obtained when the transformation was performed in DME/H2O at 80 °C with 4 equiv of the boronic acid. The results discussed herein extend the scope of the addition of arylboronic acids to highly activated diketones and ketoesters. The products of the reaction are useful in the synthesis of natural products containing oxygenation next to esters or ketones.

AB - The metal complex Rh(acac)(CO)2 in the presence of dicyclohexylphenylphosphine provides a useful catalyst system for the addition of boronic acids to 1,2-diketones and 1,2-ketoesters. The best yields were obtained when the transformation was performed in DME/H2O at 80 °C with 4 equiv of the boronic acid. The results discussed herein extend the scope of the addition of arylboronic acids to highly activated diketones and ketoesters. The products of the reaction are useful in the synthesis of natural products containing oxygenation next to esters or ketones.

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JO - Tetrahedron Letters

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Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters

Abstract

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