Synthetic Access to Pentacene-Silylene Adducts via Dehydrogenative Silylation of a 5,14-Dihydropentacene with a Stable Silylene

Taichi Koike; Takeaki Iwamoto

doi:10.1002/ejoc.202100296

Synthetic Access to Pentacene-Silylene Adducts via Dehydrogenative Silylation of a 5,14-Dihydropentacene with a Stable Silylene

Taichi Koike, Takeaki Iwamoto

SCI - Chemistry

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

Abstract

Utility of a thermally stable divalent silicon species (silylene) toward the dehydroaromatization of a dihydropentacene is demonstrated. The reaction of a cyclic (alkyl)(amino)silylene with 6,13-dipropyl-5,14-dihydropentacene afforded the corresponding pentacene-silylene adducts. The reaction likely proceeds through a combination of 1,4-dehydrogenation and (1+4) cycloaddition of the silylene towards the dihydropentacene.

Original language	English
Pages (from-to)	2219-2222
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.202100296
Publication status	Published - 2021 Apr 22

Keywords

Aromatic compounds
Dehydrogenation
Main group elements
Silicon
Silylenes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.202100296

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title = "Synthetic Access to Pentacene-Silylene Adducts via Dehydrogenative Silylation of a 5,14-Dihydropentacene with a Stable Silylene",

abstract = "Utility of a thermally stable divalent silicon species (silylene) toward the dehydroaromatization of a dihydropentacene is demonstrated. The reaction of a cyclic (alkyl)(amino)silylene with 6,13-dipropyl-5,14-dihydropentacene afforded the corresponding pentacene-silylene adducts. The reaction likely proceeds through a combination of 1,4-dehydrogenation and (1+4) cycloaddition of the silylene towards the dihydropentacene.",

keywords = "Aromatic compounds, Dehydrogenation, Main group elements, Silicon, Silylenes",

author = "Taichi Koike and Takeaki Iwamoto",

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doi = "10.1002/ejoc.202100296",

language = "English",

volume = "2021",

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T1 - Synthetic Access to Pentacene-Silylene Adducts via Dehydrogenative Silylation of a 5,14-Dihydropentacene with a Stable Silylene

AU - Koike, Taichi

AU - Iwamoto, Takeaki

N1 - Funding Information: This work was supported by the JSPS KAKENHI (grant JP20J21205 to T. K.; JP15K13634 to T. I.) and the Mitsubishi Foundation research grant in the natural sciences (201910006 to T. I.). Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/4/22

Y1 - 2021/4/22

N2 - Utility of a thermally stable divalent silicon species (silylene) toward the dehydroaromatization of a dihydropentacene is demonstrated. The reaction of a cyclic (alkyl)(amino)silylene with 6,13-dipropyl-5,14-dihydropentacene afforded the corresponding pentacene-silylene adducts. The reaction likely proceeds through a combination of 1,4-dehydrogenation and (1+4) cycloaddition of the silylene towards the dihydropentacene.

AB - Utility of a thermally stable divalent silicon species (silylene) toward the dehydroaromatization of a dihydropentacene is demonstrated. The reaction of a cyclic (alkyl)(amino)silylene with 6,13-dipropyl-5,14-dihydropentacene afforded the corresponding pentacene-silylene adducts. The reaction likely proceeds through a combination of 1,4-dehydrogenation and (1+4) cycloaddition of the silylene towards the dihydropentacene.

KW - Aromatic compounds

KW - Dehydrogenation

KW - Main group elements

KW - Silicon

KW - Silylenes

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JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

SN - 0075-4617

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Synthetic Access to Pentacene-Silylene Adducts via Dehydrogenative Silylation of a 5,14-Dihydropentacene with a Stable Silylene

Abstract

Keywords

ASJC Scopus subject areas

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