Palladium-Catalyzed Carbothiolation via Trapping of the σ-Alkyl Palladium Intermediate with RSTIPS

Yosuke Hosoya; Ikumi Kobayashi; Kota Mizoguchi; Masahisa Nakada

doi:10.1021/acs.orglett.9b03046

Palladium-Catalyzed Carbothiolation via Trapping of the σ-Alkyl Palladium Intermediate with RSTIPS

Yosuke Hosoya, Ikumi Kobayashi, Kota Mizoguchi, Masahisa Nakada

School of Advanced Science and Engineering

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

1 Citation (Scopus)

Abstract

A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs₂CO₃, (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.

Original language	English
Pages (from-to)	8280-8284
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.9b03046
Publication status	Published - 2019 Oct 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs2CO3, (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.",

author = "Yosuke Hosoya and Ikumi Kobayashi and Kota Mizoguchi and Masahisa Nakada",

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T1 - Palladium-Catalyzed Carbothiolation via Trapping of the σ-Alkyl Palladium Intermediate with RSTIPS

AU - Hosoya, Yosuke

AU - Kobayashi, Ikumi

AU - Mizoguchi, Kota

AU - Nakada, Masahisa

PY - 2019/10/18

Y1 - 2019/10/18

N2 - A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs2CO3, (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.

AB - A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs2CO3, (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.

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JO - Organic Letters

JF - Organic Letters

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