Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes

Hyeon Jin Mun; Eun Young Seong; Kwang Hyun Ahn; Eun Joo Kang

doi:10.1021/acs.joc.7b02672

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes

Hyeon Jin Mun
, Eun Young Seong
, Kwang Hyun Ahn
, Eun Joo Kang

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

25 Citations (Scopus)

Abstract

The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.

Original language	English
Pages (from-to)	1196-1203
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.7b02672
Publication status	Published - 2 Feb 2018

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© 2017 American Chemical Society.

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title = "Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes",

abstract = "The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.",

author = "Mun, \{Hyeon Jin\} and Seong, \{Eun Young\} and Ahn, \{Kwang Hyun\} and Kang, \{Eun Joo\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.joc.7b02672",

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T1 - Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes

AU - Mun, Hyeon Jin

AU - Seong, Eun Young

AU - Ahn, Kwang Hyun

AU - Kang, Eun Joo

PY - 2018/2/2

Y1 - 2018/2/2

N2 - The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.

AB - The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.

UR - https://www.scopus.com/pages/publications/85041569341

U2 - 10.1021/acs.joc.7b02672

DO - 10.1021/acs.joc.7b02672

M3 - Article

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AN - SCOPUS:85041569341

SN - 0022-3263

VL - 83

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EP - 1203

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes

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