An Iron-Based Dehydration Catalyst for Selective Formation of Styrene

Nachtigall, Olaf; VanderWeide, Andrew I.; Brennessel, William W.; Jones, William D.

doi:10.1021/acscatal.1c03037

Title: An Iron-Based Dehydration Catalyst for Selective Formation of Styrene

Journal Article · 23 August 2021 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.1c03037 · OSTI ID:1817908

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Univ. of Rochester, NY (United States); Univ. of California, Irvine, CA (United States); University of Rochester
Univ. of Rochester, NY (United States)

In this work, we report the synthesis and crystal structure of [Fe(OTf)₂(FOX)] (A). This robust iron(II) complex was successfully applied as a homogeneous catalyst for the dehydration of 1-phenylethanol to styrene. Even at low catalyst loadings and moderate reaction temperatures, A showed a high catalytic efficiency. It was found to selectively activate the benzylic alcohol group of 1-phenylethanol. This is challenging since the vinyl system of styrene is highly reactive. In contrast to most of the other dehydration processes, the use of a Brønsted acid was not necessary. Furthermore, mechanistic insights into this E₁-type transformation and its competing S_N1-type side reactions are reported. [Fe(^cHexOH)(OTf)(FOX)][OTf] (B), an alcohol adduct of A, [Fe(H₂O)₂(FOX)][OTf]₂ (C), the completely hydrated derivative of A, and [μ-O{Fe(OTf)(FOX)}₂][OTf]₂ (D), a dinuclear oxidation product of A, were also characterized and are discussed.

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Research Organization:: Univ. of Rochester, NY (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: SC0020230

OSTI ID:: 1817908

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Vol. 11; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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02 PETROLEUM
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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CCDC 2086601: Experimental Crystal Structure Determination Olaf, Nachtigall,; I., VanderWeide, Andrew; W., Brennessel, William https://doi.org/10.5517/ccdc.csd.cc2818qb The current record is supplemented by this dataset	dataset	January 2021
CCDC 2086602: Experimental Crystal Structure Determination Olaf, Nachtigall,; I., VanderWeide, Andrew; W., Brennessel, William https://doi.org/10.5517/ccdc.csd.cc2818rc The current record is supplemented by this dataset	dataset	January 2021
CCDC 2086603: Experimental Crystal Structure Determination Olaf, Nachtigall,; I., VanderWeide, Andrew; W., Brennessel, William https://doi.org/10.5517/ccdc.csd.cc2818sd The current record is supplemented by this dataset	dataset	January 2021
CCDC 2086604: Experimental Crystal Structure Determination Olaf, Nachtigall,; I., VanderWeide, Andrew; W., Brennessel, William https://doi.org/10.5517/ccdc.csd.cc2818tf The current record is supplemented by this dataset	dataset	January 2021

Title: An Iron-Based Dehydration Catalyst for Selective Formation of Styrene

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