Pd(II)-Catalyzed Direct Dehydrogenative Mono- And Diolefination of Selenophenes

Shi Yen Chen; Santosh K. Sahoo; Ching Li Huang; Tung Hsien Chan; Yen Ju Cheng

doi:10.1021/acs.orglett.0c00506

Pd(II)-Catalyzed Direct Dehydrogenative Mono- And Diolefination of Selenophenes

Shi Yen Chen, Santosh K. Sahoo, Ching Li Huang, Tung Hsien Chan, Yen Ju Cheng^*

^*Corresponding author for this work

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

12 Scopus citations

Abstract

Pd(II)-catalyzed dehydrogenative Heck olefination of selenophenes with a broad olefinic substrate scope and high functional group tolerance is demonstrated. Carbonyl-substituted and phenyl-substituted olefins with electron-donating (D) and electron-accepting (A) groups can be regioselectively installed at C2 of the selenophene. The 2-olefinated selenophenes can subsequently undergo a second oxidative olefination to rapidly produce a new class of symmetrical D-π-D or unsymmetrical D-π-A 2,5-diolefinated selenophene materials.

Original language	English
Pages (from-to)	2318-2322
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.0c00506
State	Published - 20 Mar 2020

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title = "Pd(II)-Catalyzed Direct Dehydrogenative Mono- And Diolefination of Selenophenes",

abstract = "Pd(II)-catalyzed dehydrogenative Heck olefination of selenophenes with a broad olefinic substrate scope and high functional group tolerance is demonstrated. Carbonyl-substituted and phenyl-substituted olefins with electron-donating (D) and electron-accepting (A) groups can be regioselectively installed at C2 of the selenophene. The 2-olefinated selenophenes can subsequently undergo a second oxidative olefination to rapidly produce a new class of symmetrical D-π-D or unsymmetrical D-π-A 2,5-diolefinated selenophene materials.",

author = "Chen, {Shi Yen} and Sahoo, {Santosh K.} and Huang, {Ching Li} and Chan, {Tung Hsien} and Cheng, {Yen Ju}",

year = "2020",

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day = "20",

doi = "10.1021/acs.orglett.0c00506",

language = "English",

volume = "22",

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journal = "Organic Letters",

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T1 - Pd(II)-Catalyzed Direct Dehydrogenative Mono- And Diolefination of Selenophenes

AU - Chen, Shi Yen

AU - Sahoo, Santosh K.

AU - Huang, Ching Li

AU - Chan, Tung Hsien

AU - Cheng, Yen Ju

PY - 2020/3/20

Y1 - 2020/3/20

N2 - Pd(II)-catalyzed dehydrogenative Heck olefination of selenophenes with a broad olefinic substrate scope and high functional group tolerance is demonstrated. Carbonyl-substituted and phenyl-substituted olefins with electron-donating (D) and electron-accepting (A) groups can be regioselectively installed at C2 of the selenophene. The 2-olefinated selenophenes can subsequently undergo a second oxidative olefination to rapidly produce a new class of symmetrical D-π-D or unsymmetrical D-π-A 2,5-diolefinated selenophene materials.

AB - Pd(II)-catalyzed dehydrogenative Heck olefination of selenophenes with a broad olefinic substrate scope and high functional group tolerance is demonstrated. Carbonyl-substituted and phenyl-substituted olefins with electron-donating (D) and electron-accepting (A) groups can be regioselectively installed at C2 of the selenophene. The 2-olefinated selenophenes can subsequently undergo a second oxidative olefination to rapidly produce a new class of symmetrical D-π-D or unsymmetrical D-π-A 2,5-diolefinated selenophene materials.

UR - http://www.scopus.com/inward/record.url?scp=85081247966&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c00506

DO - 10.1021/acs.orglett.0c00506

M3 - Article

C2 - 32118452

AN - SCOPUS:85081247966

SN - 1523-7060

VL - 22

SP - 2318

EP - 2322

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Pd(II)-Catalyzed Direct Dehydrogenative Mono- And Diolefination of Selenophenes

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