Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins

Bill Morandi; Zachary K. Wickens; Robert H. Grubbs

doi:10.1002/ange.201209541

Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins

Bill Morandi, Zachary K. Wickens, Robert H. Grubbs

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

85 Scopus citations

Abstract

Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.

Original language	English (US)
Pages (from-to)	3016-3020
Number of pages	5
Journal	Angewandte Chemie
Volume	125
Issue number	10
DOIs	https://doi.org/10.1002/ange.201209541
State	Published - Jan 16 2013
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Scott Virgil and the Caltech Center for Catalysis for technical assistance. We gratefully acknowledge financial support from King Abdullah University of Science and Technology Center in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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10.1002/ange.201209541

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title = "Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins",

abstract = "Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.",

author = "Bill Morandi and Wickens, {Zachary K.} and Grubbs, {Robert H.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Scott Virgil and the Caltech Center for Catalysis for technical assistance. We gratefully acknowledge financial support from King Abdullah University of Science and Technology Center in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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AU - Morandi, Bill

AU - Wickens, Zachary K.

AU - Grubbs, Robert H.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Scott Virgil and the Caltech Center for Catalysis for technical assistance. We gratefully acknowledge financial support from King Abdullah University of Science and Technology Center in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2013/1/16

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N2 - Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.

AB - Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.

UR - http://hdl.handle.net/10754/599374

UR - http://doi.wiley.com/10.1002/ange.201209541

U2 - 10.1002/ange.201209541

DO - 10.1002/ange.201209541

M3 - Article

SN - 0044-8249

VL - 125

SP - 3016

EP - 3020

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 10

ER -

Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins

Abstract

Bibliographical note

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