1,8-Di(2-ethynylaryl)biphenylenes: Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement

Hsiang Han Chen; Chih Hsuan Liu; Wei Ting Ou; Kuan Hsun Huang; Chia Jung Yang; Mu-Jeng Cheng; Yao Ting Wu

doi:10.1021/acs.orglett.5c04302

1,8-Di(2-ethynylaryl)biphenylenes: Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement

Hsiang Han Chen
, Chih Hsuan Liu
, Wei Ting Ou
, Kuan Hsun Huang
, Chia Jung Yang
, Mu-Jeng Cheng
, Yao Ting Wu

Department of Chemistry

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

Abstract

A cascade reaction for 1,8-dibromobiphenylene A with arylboronic acid B toward an unusual product C was comprehensively investigated. The initially formed Suzuki product D underwent an unprecedented palladium-catalyzed cycloisomerization, yielding E with a unique 5–8–5-membered ring framework. In most cases, E proceeded via thermal rearrangement to form C. This work also examined the scope and limitations of the cascade reaction, probed its mechanism, and verified the structures of C and E by X-ray crystallography.

Original language	English
Pages (from-to)	12886-12891
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.5c04302
Publication status	Published - 2025 Nov 21

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c04302

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title = "1,8-Di(2-ethynylaryl)biphenylenes: Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement",

abstract = "A cascade reaction for 1,8-dibromobiphenylene A with arylboronic acid B toward an unusual product C was comprehensively investigated. The initially formed Suzuki product D underwent an unprecedented palladium-catalyzed cycloisomerization, yielding E with a unique 5–8–5-membered ring framework. In most cases, E proceeded via thermal rearrangement to form C. This work also examined the scope and limitations of the cascade reaction, probed its mechanism, and verified the structures of C and E by X-ray crystallography.",

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doi = "10.1021/acs.orglett.5c04302",

language = "English",

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T1 - 1,8-Di(2-ethynylaryl)biphenylenes

T2 - Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement

AU - Chen, Hsiang Han

AU - Liu, Chih Hsuan

AU - Ou, Wei Ting

AU - Huang, Kuan Hsun

AU - Yang, Chia Jung

AU - Cheng, Mu-Jeng

AU - Wu, Yao Ting

PY - 2025/11/21

Y1 - 2025/11/21

N2 - A cascade reaction for 1,8-dibromobiphenylene A with arylboronic acid B toward an unusual product C was comprehensively investigated. The initially formed Suzuki product D underwent an unprecedented palladium-catalyzed cycloisomerization, yielding E with a unique 5–8–5-membered ring framework. In most cases, E proceeded via thermal rearrangement to form C. This work also examined the scope and limitations of the cascade reaction, probed its mechanism, and verified the structures of C and E by X-ray crystallography.

AB - A cascade reaction for 1,8-dibromobiphenylene A with arylboronic acid B toward an unusual product C was comprehensively investigated. The initially formed Suzuki product D underwent an unprecedented palladium-catalyzed cycloisomerization, yielding E with a unique 5–8–5-membered ring framework. In most cases, E proceeded via thermal rearrangement to form C. This work also examined the scope and limitations of the cascade reaction, probed its mechanism, and verified the structures of C and E by X-ray crystallography.

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SN - 1523-7060

VL - 27

SP - 12886

EP - 12891

JO - Organic Letters

JF - Organic Letters

IS - 46

ER -

1,8-Di(2-ethynylaryl)biphenylenes: Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement

Abstract

All Science Journal Classification (ASJC) codes

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