Lithium promoted mesoporous manganese oxide catalyzed oxidation of allyl ethers

Biswanath Dutta, Ryan Clarke, Sumathy Raman, Timothy D. Shaffer, Laura Achola, Partha Nandi () and Steven L. Suib ()
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Biswanath Dutta: University of Connecticut, U-3060
Ryan Clarke: University of Connecticut, U-3060
Sumathy Raman: Corporate Strategic Research, ExxonMobil
Timothy D. Shaffer: Corporate Strategic Research, ExxonMobil
Laura Achola: University of Connecticut, U-3060
Partha Nandi: Corporate Strategic Research, ExxonMobil
Steven L. Suib: University of Connecticut, U-3060

Nature Communications, 2019, vol. 10, issue 1, 1-6

Abstract: Abstract Herein we report the first example of the catalytic aerobic partial oxidation of allyl ether to its acrylate ester derivative. Many partial oxidations often need an expensive oxidant such as peroxides or other species to drive such reactions. In addition, selective generation of esters using porous catalysts has been elusive. This reaction is catalyzed by a Li ion promoted mesoporous manganese oxide (meso-Mn2O3) under mild conditions with no precious metals, a reusable heterogeneous catalyst, and easy isolation. This process is very attractive for the oxidation of allyl ethers. We report on the catalytic activity, selectivity, and scope of the reaction. In the best cases presented, almost complete conversion of allyl ether with near complete chemo-selectivity towards acrylate ester derivatives is observed. Based on results from controlled experiments, we propose a possible reaction mechanism for the case in which N-hydroxyphthalimide (NHPI) is used in combination with trichloroacetonitrile (CCl3CN).

Date: 2019
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DOI: 10.1038/s41467-019-08619-x

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