Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination

Shunsuke Chiba; Line Zhang; Stephen Sanjaya; Gim Yean Ang

doi:10.1016/j.tet.2010.05.029

Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination

Shunsuke Chiba^*, Line Zhang, Stephen Sanjaya, Gim Yean Ang

^*Corresponding author for this work

Nanyang Technological University

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

23 Citations (Scopus)

Abstract

α-Aryl-a-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2 3-disubstituted indole derivatives catalyzed by PdCl₂(MeCN)₂ in the presence of MgO as a base. The reaction is supposed to proceed via intramolecular aromatic C-H amination of a vinyl nitrene-palladium intermediate.

Original language	English
Pages (from-to)	5692-5700
Number of pages	9
Journal	Tetrahedron
Volume	66
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2010.05.029
Publication status	Published - Jul 24 2010
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Indoles Oximes C-H amination Vinyl nitrene Palladium catalysts

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10.1016/j.tet.2010.05.029

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title = "Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination",

abstract = "α-Aryl-a-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2 3-disubstituted indole derivatives catalyzed by PdCl2(MeCN)2 in the presence of MgO as a base. The reaction is supposed to proceed via intramolecular aromatic C-H amination of a vinyl nitrene-palladium intermediate.",

keywords = "Indoles Oximes C-H amination Vinyl nitrene Palladium catalysts",

author = "Shunsuke Chiba and Line Zhang and Stephen Sanjaya and Ang, {Gim Yean}",

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T1 - Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination

AU - Chiba, Shunsuke

AU - Zhang, Line

AU - Sanjaya, Stephen

AU - Ang, Gim Yean

PY - 2010/7/24

Y1 - 2010/7/24

N2 - α-Aryl-a-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2 3-disubstituted indole derivatives catalyzed by PdCl2(MeCN)2 in the presence of MgO as a base. The reaction is supposed to proceed via intramolecular aromatic C-H amination of a vinyl nitrene-palladium intermediate.

AB - α-Aryl-a-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2 3-disubstituted indole derivatives catalyzed by PdCl2(MeCN)2 in the presence of MgO as a base. The reaction is supposed to proceed via intramolecular aromatic C-H amination of a vinyl nitrene-palladium intermediate.

KW - Indoles Oximes C-H amination Vinyl nitrene Palladium catalysts

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U2 - 10.1016/j.tet.2010.05.029

DO - 10.1016/j.tet.2010.05.029

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SN - 0040-4020

VL - 66

SP - 5692

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JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination

Abstract

ASJC Scopus Subject Areas

Keywords

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