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

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

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Hosoya, Y., Kobayashi, I., Mizoguchi, K., & Nakada, M. (2019). Palladium-Catalyzed Carbothiolation via Trapping of the σ-Alkyl Palladium Intermediate with RSTIPS. Organic Letters, 21(20), 8280-8284. https://doi.org/10.1021/acs.orglett.9b03046

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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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Access to Document

10.1021/acs.orglett.9b03046