Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

Yosuke Hosoya; Kota Mizoguchi; Honoka Yasukochi; Masahisa Nakada

doi:10.1055/a-1733-6073

Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

Yosuke Hosoya, Kota Mizoguchi, Honoka Yasukochi, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

1 Citation (Scopus)

Abstract

We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.

Original language	English
Pages (from-to)	495-501
Number of pages	7
Journal	Synlett
Volume	33
Issue number	5
DOIs	https://doi.org/10.1055/a-1733-6073
Publication status	Published - 2022 Mar 17

Keywords

acyl fluorides
palladium catalysis
thiocarbonylation
thioesters
thioethers

ASJC Scopus subject areas

Organic Chemistry

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title = "Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers",

abstract = "We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.",

keywords = "acyl fluorides, palladium catalysis, thiocarbonylation, thioesters, thioethers",

author = "Yosuke Hosoya and Kota Mizoguchi and Honoka Yasukochi and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by JSPS KAKENHI Grant Number JP19H02725 and a Waseda University Grant for Special Research Projects.JapanSocietyforthePomotionofScienceJP15H05841)WaedaUniveiyt Publisher Copyright: {\textcopyright} 2022 Georg Thieme Verlag. All rights reserved.",

year = "2022",

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doi = "10.1055/a-1733-6073",

language = "English",

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T1 - Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

AU - Hosoya, Yosuke

AU - Mizoguchi, Kota

AU - Yasukochi, Honoka

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by JSPS KAKENHI Grant Number JP19H02725 and a Waseda University Grant for Special Research Projects.JapanSocietyforthePomotionofScienceJP15H05841)WaedaUniveiyt Publisher Copyright: © 2022 Georg Thieme Verlag. All rights reserved.

PY - 2022/3/17

Y1 - 2022/3/17

N2 - We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.

AB - We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.

KW - acyl fluorides

KW - palladium catalysis

KW - thiocarbonylation

KW - thioesters

KW - thioethers

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U2 - 10.1055/a-1733-6073

DO - 10.1055/a-1733-6073

M3 - Article

AN - SCOPUS:85124381523

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VL - 33

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JO - Synlett

JF - Synlett

IS - 5

ER -

Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

Abstract

Keywords

ASJC Scopus subject areas

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