Lithium promoted mesoporous manganese oxide catalyzed oxidation of allyl ethers

Dutta, Biswanath; Clarke, Ryan; Raman, Sumathy; Shaffer, Timothy D.; Achola, Laura; Nandi, Partha; Suib, Steven L.

doi:10.1038/s41467-019-08619-x

Title: Lithium promoted mesoporous manganese oxide catalyzed oxidation of allyl ethers

Journal Article · Fri Feb 08 00:00:00 EST 2019 · Nature Communications

DOI:https://doi.org/10.1038/s41467-019-08619-x· OSTI ID:1598195

Dutta, Biswanath ^[1];

^[1]; Raman, Sumathy ^[2]; Shaffer, Timothy D. ^[2]; Achola, Laura ^[1]; Nandi, Partha ^[2]; Suib, Steven L. ^[1]

Univ. of Connecticut, Storrs, CT (United States)
ExxonMobil, Annandale, NJ (United States)

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).

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Research Organization:: Univ. of Connecticut, Storrs, CT (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

Contributing Organization:: ExxonMobil Research and Engineering Company

Grant/Contract Number:: FG02-86ER13622

OSTI ID:: 1598195

Journal Information:: Nature Communications, Vol. 10, Issue 1; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 16 works

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Mechanistic insights into N -hydroxyphthalimide modified graphitic carbon nitride boosted photocatalytic hydrogen production Ma, Liu-Bo; Liang, Kuang; Wang, Gang Catalysis Science & Technology, Vol. 9, Issue 19 https://doi.org/10.1039/c9cy01340g	journal	January 2019
Continuous flow/waste-minimized synthesis of benzoxazoles catalysed by heterogeneous manganese systems Ferlin, Francesco; van der Hulst, Mitchell K.; Santoro, Stefano Green Chemistry, Vol. 21, Issue 19 https://doi.org/10.1039/c9gc01641d	journal	January 2019
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Mn-catalyzed radical initiated domino transformation of alkynylated cyclohexadienones with TMSN ₃ and O ₂ to bicyclic azido alcohols Pal, Pranesh; Mainkar, Prathama S.; Nayani, Kiranmai Chemical Communications, Vol. 56, Issue 23 https://doi.org/10.1039/d0cc00102c	journal	January 2020
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