Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives: Syntheses, Structural Analyses, and Properties

Po Ting Chen; Chia Ling Yu; Min Hsiu Shen; Mu Jeng Cheng; Yao Ting Wu; Hsiu Fu Hsu

doi:10.1021/acs.orglett.2c01778

Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives: Syntheses, Structural Analyses, and Properties

Po Ting Chen, Chia Ling Yu, Min Hsiu Shen, Mu Jeng Cheng, Yao Ting Wu, Hsiu Fu Hsu

Department of Chemistry

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

3 Citations (Scopus)

Abstract

This investigation demonstrates that a series of (highly) substituted acephenanthrylenes (APs) 2, benzo[l]acephenanthrylene 3, and dicyclopenta[cd,mn]pyrene 4 are easily prepared by palladium-catalyzed cycloaromatization of 2,3-diethynylbiphenyls 1. The first nonpyrolysis synthesis of 4 by two-fold cycloaromatization was achieved in a high yield. This synthetic protocol has two crucial advantages: facile introduction of various substituents and efficient extension of the AP backbone.

Original language	English
Pages (from-to)	4778-4782
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	26
DOIs	https://doi.org/10.1021/acs.orglett.2c01778
Publication status	Published - 2022 Jul 8

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c01778

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title = "Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives: Syntheses, Structural Analyses, and Properties",

abstract = "This investigation demonstrates that a series of (highly) substituted acephenanthrylenes (APs) 2, benzo[l]acephenanthrylene 3, and dicyclopenta[cd,mn]pyrene 4 are easily prepared by palladium-catalyzed cycloaromatization of 2,3-diethynylbiphenyls 1. The first nonpyrolysis synthesis of 4 by two-fold cycloaromatization was achieved in a high yield. This synthetic protocol has two crucial advantages: facile introduction of various substituents and efficient extension of the AP backbone.",

author = "Chen, {Po Ting} and Yu, {Chia Ling} and Shen, {Min Hsiu} and Cheng, {Mu Jeng} and Wu, {Yao Ting} and Hsu, {Hsiu Fu}",

note = "Funding Information: This work was supported by the Ministry of Science and Technology of Taiwan. The Instrumentation Center at National Tsing Hua University (X-ray crystallography) and the National Center for High-performance Computing (computational resources) are also acknowledged. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

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doi = "10.1021/acs.orglett.2c01778",

language = "English",

volume = "24",

pages = "4778--4782",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives

T2 - Syntheses, Structural Analyses, and Properties

AU - Chen, Po Ting

AU - Yu, Chia Ling

AU - Shen, Min Hsiu

AU - Cheng, Mu Jeng

AU - Wu, Yao Ting

AU - Hsu, Hsiu Fu

N1 - Funding Information: This work was supported by the Ministry of Science and Technology of Taiwan. The Instrumentation Center at National Tsing Hua University (X-ray crystallography) and the National Center for High-performance Computing (computational resources) are also acknowledged. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/7/8

Y1 - 2022/7/8

N2 - This investigation demonstrates that a series of (highly) substituted acephenanthrylenes (APs) 2, benzo[l]acephenanthrylene 3, and dicyclopenta[cd,mn]pyrene 4 are easily prepared by palladium-catalyzed cycloaromatization of 2,3-diethynylbiphenyls 1. The first nonpyrolysis synthesis of 4 by two-fold cycloaromatization was achieved in a high yield. This synthetic protocol has two crucial advantages: facile introduction of various substituents and efficient extension of the AP backbone.

AB - This investigation demonstrates that a series of (highly) substituted acephenanthrylenes (APs) 2, benzo[l]acephenanthrylene 3, and dicyclopenta[cd,mn]pyrene 4 are easily prepared by palladium-catalyzed cycloaromatization of 2,3-diethynylbiphenyls 1. The first nonpyrolysis synthesis of 4 by two-fold cycloaromatization was achieved in a high yield. This synthetic protocol has two crucial advantages: facile introduction of various substituents and efficient extension of the AP backbone.

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JO - Organic Letters

JF - Organic Letters

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ER -

Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives: Syntheses, Structural Analyses, and Properties

Abstract

All Science Journal Classification (ASJC) codes

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