Palladium-Catalyzed Direct Cross-Dehydrogenative Alkynylation of Selenophenes

Shi Yen Chen; Yan Hsiang Tseng; Chia Fang Lu; Chun Yao Chuang; Yen Ju Cheng

doi:10.1002/adsc.202100741

Palladium-Catalyzed Direct Cross-Dehydrogenative Alkynylation of Selenophenes

Shi Yen Chen, Yan Hsiang Tseng, Chia Fang Lu, Chun Yao Chuang, Yen Ju Cheng^*

^*Corresponding author for this work

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

1 Scopus citations

Abstract

A palladium-catalyzed (Pd(PPh₃)₄/Ag₂O/PivOH) C₂-regioselective direct dehydrogenative alkynylation of unsubstituted selenophene was achieved. The selenophenes substituted with R¹ groups at 2-position can be C₅-alkynylated with a variety of 4-substituted phenylacetylenes (R² groups). The R¹ and R² can be either electron-withdrawing or electron-donating groups, demonstrating a wide range of substrate scope with various functional group tolerance. The mono/C₂-alkynylated selenophenes can subsequently undergo the second direct alkynylation at C₅-position to afford symmetrical or unsymmetrical donor-π-acceptor 2,5-dialkynylated selenophenes. (Figure presented.).

Original language	English
Pages (from-to)	4526-4531
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	19
DOIs	https://doi.org/10.1002/adsc.202100741
State	Published - 5 Oct 2021

Keywords

C−H activation
dehydrogenative alkynylation
Pd-catalyzed
selenophene

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title = "Palladium-Catalyzed Direct Cross-Dehydrogenative Alkynylation of Selenophenes",

abstract = "A palladium-catalyzed (Pd(PPh3)4/Ag2O/PivOH) C2-regioselective direct dehydrogenative alkynylation of unsubstituted selenophene was achieved. The selenophenes substituted with R1 groups at 2-position can be C5-alkynylated with a variety of 4-substituted phenylacetylenes (R2 groups). The R1 and R2 can be either electron-withdrawing or electron-donating groups, demonstrating a wide range of substrate scope with various functional group tolerance. The mono/C2-alkynylated selenophenes can subsequently undergo the second direct alkynylation at C5-position to afford symmetrical or unsymmetrical donor-π-acceptor 2,5-dialkynylated selenophenes. (Figure presented.).",

keywords = "C−H activation, dehydrogenative alkynylation, Pd-catalyzed, selenophene",

author = "Chen, {Shi Yen} and Tseng, {Yan Hsiang} and Lu, {Chia Fang} and Chuang, {Chun Yao} and Cheng, {Yen Ju}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = oct,

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doi = "10.1002/adsc.202100741",

language = "English",

volume = "363",

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journal = "Advanced Synthesis and Catalysis",

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T1 - Palladium-Catalyzed Direct Cross-Dehydrogenative Alkynylation of Selenophenes

AU - Chen, Shi Yen

AU - Tseng, Yan Hsiang

AU - Lu, Chia Fang

AU - Chuang, Chun Yao

AU - Cheng, Yen Ju

PY - 2021/10/5

Y1 - 2021/10/5

N2 - A palladium-catalyzed (Pd(PPh3)4/Ag2O/PivOH) C2-regioselective direct dehydrogenative alkynylation of unsubstituted selenophene was achieved. The selenophenes substituted with R1 groups at 2-position can be C5-alkynylated with a variety of 4-substituted phenylacetylenes (R2 groups). The R1 and R2 can be either electron-withdrawing or electron-donating groups, demonstrating a wide range of substrate scope with various functional group tolerance. The mono/C2-alkynylated selenophenes can subsequently undergo the second direct alkynylation at C5-position to afford symmetrical or unsymmetrical donor-π-acceptor 2,5-dialkynylated selenophenes. (Figure presented.).

AB - A palladium-catalyzed (Pd(PPh3)4/Ag2O/PivOH) C2-regioselective direct dehydrogenative alkynylation of unsubstituted selenophene was achieved. The selenophenes substituted with R1 groups at 2-position can be C5-alkynylated with a variety of 4-substituted phenylacetylenes (R2 groups). The R1 and R2 can be either electron-withdrawing or electron-donating groups, demonstrating a wide range of substrate scope with various functional group tolerance. The mono/C2-alkynylated selenophenes can subsequently undergo the second direct alkynylation at C5-position to afford symmetrical or unsymmetrical donor-π-acceptor 2,5-dialkynylated selenophenes. (Figure presented.).

KW - C−H activation

KW - dehydrogenative alkynylation

KW - Pd-catalyzed

KW - selenophene

UR - http://www.scopus.com/inward/record.url?scp=85112857849&partnerID=8YFLogxK

U2 - 10.1002/adsc.202100741

DO - 10.1002/adsc.202100741

M3 - Article

AN - SCOPUS:85112857849

SN - 1615-4150

VL - 363

SP - 4526

EP - 4531

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 19

ER -

Palladium-Catalyzed Direct Cross-Dehydrogenative Alkynylation of Selenophenes

Abstract

Keywords

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