Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether

Takashi Okitsu; Yoshiki Shinohara; Haoran Luo; Manabu Hatano; Takayuki Yakura

doi:10.1002/asia.202301031

Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether

Takashi Okitsu^*, Yoshiki Shinohara, Haoran Luo, Manabu Hatano, Takayuki Yakura^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

1 Scopus citations

Abstract

Dearomative intramolecular Diels–Alder/sulfur extrusion reaction of thiophenes with alkynes successfully afforded fluoranthenes in moderate to excellent yields. The proximity of both reactive sites fixed at the peri-position of naphthalene would play an important role in the progress of this reaction. Tri(o-tolyl)phosphine effectively suppressed the side reactions as a sulfur scavenger.

Original language	English
Article number	e202301031
Journal	Chemistry - An Asian Journal
Volume	19
Issue number	4
DOIs	https://doi.org/10.1002/asia.202301031
State	Published - 2024/02/16

Keywords

alkyne
dearomatization
Diels–Alder
fluoranthene
thiophene

ASJC Scopus subject areas

Biochemistry
General Chemistry
Organic Chemistry

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10.1002/asia.202301031

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title = "Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether",

abstract = "Dearomative intramolecular Diels–Alder/sulfur extrusion reaction of thiophenes with alkynes successfully afforded fluoranthenes in moderate to excellent yields. The proximity of both reactive sites fixed at the peri-position of naphthalene would play an important role in the progress of this reaction. Tri(o-tolyl)phosphine effectively suppressed the side reactions as a sulfur scavenger.",

keywords = "alkyne, dearomatization, Diels–Alder, fluoranthene, thiophene",

author = "Takashi Okitsu and Yoshiki Shinohara and Haoran Luo and Manabu Hatano and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

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T1 - Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether

AU - Okitsu, Takashi

AU - Shinohara, Yoshiki

AU - Luo, Haoran

AU - Hatano, Manabu

AU - Yakura, Takayuki

PY - 2024/2/16

Y1 - 2024/2/16

N2 - Dearomative intramolecular Diels–Alder/sulfur extrusion reaction of thiophenes with alkynes successfully afforded fluoranthenes in moderate to excellent yields. The proximity of both reactive sites fixed at the peri-position of naphthalene would play an important role in the progress of this reaction. Tri(o-tolyl)phosphine effectively suppressed the side reactions as a sulfur scavenger.

AB - Dearomative intramolecular Diels–Alder/sulfur extrusion reaction of thiophenes with alkynes successfully afforded fluoranthenes in moderate to excellent yields. The proximity of both reactive sites fixed at the peri-position of naphthalene would play an important role in the progress of this reaction. Tri(o-tolyl)phosphine effectively suppressed the side reactions as a sulfur scavenger.

KW - alkyne

KW - dearomatization

KW - Diels–Alder

KW - fluoranthene

KW - thiophene

UR - http://www.scopus.com/inward/record.url?scp=85183914696&partnerID=8YFLogxK

U2 - 10.1002/asia.202301031

DO - 10.1002/asia.202301031

M3 - 学術論文

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AN - SCOPUS:85183914696

SN - 1861-4728

VL - 19

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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M1 - e202301031

ER -

Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether

Abstract

Keywords

ASJC Scopus subject areas

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