Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Takehiko Matsumura; Takashi Niwa; Masahisa Nakada

doi:10.1016/j.tetlet.2012.06.002

Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Takehiko Matsumura, Takashi Niwa, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

38 Citations (Scopus)

Abstract

The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCl, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity.

Original language	English
Pages (from-to)	4313-4316
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.002
Publication status	Published - 2012 Aug 15

Keywords

Alkyl aryl sulfide
Pd-catalyzed
Reductive cleavage
Trialkylsilyl chloride
Triethylsilane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.06.002

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title = "Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride",

abstract = "The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCl, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity.",

keywords = "Alkyl aryl sulfide, Pd-catalyzed, Reductive cleavage, Trialkylsilyl chloride, Triethylsilane",

author = "Takehiko Matsumura and Takashi Niwa and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by The Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Organic Synthesis based on Reaction Integration{\textquoteright} (No. 2105 ) and the Global COE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright} by MEXT .",

year = "2012",

month = aug,

day = "15",

doi = "10.1016/j.tetlet.2012.06.002",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

AU - Matsumura, Takehiko

AU - Niwa, Takashi

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by The Grant-in-Aid for Scientific Research on Innovative Areas ‘Organic Synthesis based on Reaction Integration’ (No. 2105 ) and the Global COE program ‘Center for Practical Chemical Wisdom’ by MEXT .

PY - 2012/8/15

Y1 - 2012/8/15

N2 - The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCl, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity.

AB - The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCl, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity.

KW - Alkyl aryl sulfide

KW - Pd-catalyzed

KW - Reductive cleavage

KW - Trialkylsilyl chloride

KW - Triethylsilane

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U2 - 10.1016/j.tetlet.2012.06.002

DO - 10.1016/j.tetlet.2012.06.002

M3 - Article

AN - SCOPUS:84864031108

SN - 0040-4039

VL - 53

SP - 4313

EP - 4316

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Abstract

Keywords

ASJC Scopus subject areas

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