Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides: Nickel catalyzed Caryl-Csp3 and Csp3Csp3 bond formations

Matthias Leiendecker; Adisak Chatupheeraphat; Magnus Rueping

doi:10.1039/c5qo00001g

Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides: Nickel catalyzed C_aryl-Csp³ and Csp³Csp³ bond formations

Matthias Leiendecker, Adisak Chatupheeraphat, Magnus Rueping^*

^*Corresponding author for this work

Physical Science and Engineering

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

17 Scopus citations

Abstract

The functionalization of C_Ar-SMe and Csp³-SMe bonds by direct exchange of the sulfur atom with an activated sp³-carbon has been developed. Reactions with LiCH₂SiMe₃ in the presence of a Nickel catalyst proceed with good yields and allow the conversion of aryl and benzyl methyl sulfides to trimethylsilylated products which are valuable precursors for the synthesis of olefins, various alcohols and amines, diols and aromatic carboxylic acids.

Original language	English (US)
Pages (from-to)	350-353
Number of pages	4
Journal	Organic Chemistry Frontiers
Volume	2
Issue number	4
DOIs	https://doi.org/10.1039/c5qo00001g
State	Published - Apr 2015

ASJC Scopus subject areas

Organic Chemistry

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title = "Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides: Nickel catalyzed Caryl-Csp3 and Csp3Csp3 bond formations",

abstract = "The functionalization of CAr-SMe and Csp3-SMe bonds by direct exchange of the sulfur atom with an activated sp3-carbon has been developed. Reactions with LiCH2SiMe3 in the presence of a Nickel catalyst proceed with good yields and allow the conversion of aryl and benzyl methyl sulfides to trimethylsilylated products which are valuable precursors for the synthesis of olefins, various alcohols and amines, diols and aromatic carboxylic acids.",

author = "Matthias Leiendecker and Adisak Chatupheeraphat and Magnus Rueping",

year = "2015",

month = apr,

doi = "10.1039/c5qo00001g",

language = "English (US)",

volume = "2",

pages = "350--353",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

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T1 - Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides

T2 - Nickel catalyzed Caryl-Csp3 and Csp3Csp3 bond formations

AU - Leiendecker, Matthias

AU - Chatupheeraphat, Adisak

AU - Rueping, Magnus

PY - 2015/4

Y1 - 2015/4

N2 - The functionalization of CAr-SMe and Csp3-SMe bonds by direct exchange of the sulfur atom with an activated sp3-carbon has been developed. Reactions with LiCH2SiMe3 in the presence of a Nickel catalyst proceed with good yields and allow the conversion of aryl and benzyl methyl sulfides to trimethylsilylated products which are valuable precursors for the synthesis of olefins, various alcohols and amines, diols and aromatic carboxylic acids.

AB - The functionalization of CAr-SMe and Csp3-SMe bonds by direct exchange of the sulfur atom with an activated sp3-carbon has been developed. Reactions with LiCH2SiMe3 in the presence of a Nickel catalyst proceed with good yields and allow the conversion of aryl and benzyl methyl sulfides to trimethylsilylated products which are valuable precursors for the synthesis of olefins, various alcohols and amines, diols and aromatic carboxylic acids.

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U2 - 10.1039/c5qo00001g

DO - 10.1039/c5qo00001g

M3 - Article

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SP - 350

EP - 353

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

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ER -

Metal catalyzed cross-coupling of aryl and benzyl methyl sulfides: Nickel catalyzed C_aryl-Csp³ and Csp³Csp³ bond formations

Abstract

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