Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent

Zongjun Qiao; Jianpeng Wei; Xuefeng Jiang

doi:10.1021/ol500112y

Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na₂S ₂O₃ as a sulfurating reagent

Zongjun Qiao
, Jianpeng Wei
, Xuefeng Jiang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

150 Scopus citations

Abstract

The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na ₂S₂O₃·5H₂O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na₂S₂O ₃·5H₂O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.

Original language	English
Pages (from-to)	1212-1215
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	4
DOIs	https://doi.org/10.1021/ol500112y
State	Published - 21 Feb 2014

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title = "Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent",

abstract = "The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.",

author = "Zongjun Qiao and Jianpeng Wei and Xuefeng Jiang",

year = "2014",

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day = "21",

doi = "10.1021/ol500112y",

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T1 - Direct cross-coupling access to diverse aromatic sulfide

T2 - Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent

AU - Qiao, Zongjun

AU - Wei, Jianpeng

AU - Jiang, Xuefeng

PY - 2014/2/21

Y1 - 2014/2/21

N2 - The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.

AB - The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.

UR - https://www.scopus.com/pages/publications/84894535890

U2 - 10.1021/ol500112y

DO - 10.1021/ol500112y

M3 - 文章

AN - SCOPUS:84894535890

SN - 1523-7060

VL - 16

SP - 1212

EP - 1215

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na₂S ₂O₃ as a sulfurating reagent

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