Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst

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

doi:10.1002/ange.201306756

Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst

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

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

87 Scopus citations

Abstract

Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

Original language	English (US)
Pages (from-to)	11467-11470
Number of pages	4
Journal	Angewandte Chemie
Volume	125
Issue number	43
DOIs	https://doi.org/10.1002/ange.201306756
State	Published - Sep 13 2013
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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10.1002/ange.201306756

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title = "Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst",

abstract = "Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.",

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

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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AU - Wickens, Zachary K.

AU - Morandi, Bill

AU - Grubbs, Robert H.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2013/9/13

Y1 - 2013/9/13

N2 - Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

AB - Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

UR - http://hdl.handle.net/10754/597486

UR - http://doi.wiley.com/10.1002/ange.201306756

U2 - 10.1002/ange.201306756

DO - 10.1002/ange.201306756

M3 - Article

SN - 0044-8249

VL - 125

SP - 11467

EP - 11470

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 43

ER -

Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst

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