Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes

Pei Chui Too; Toshiharu Noji; Ying Jie Lim; Xingwei Li; Shunsuke Chiba

doi:10.1055/s-0031-1289556

Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes

Pei Chui Too, Toshiharu Noji, Ying Jie Lim, Xingwei Li^*, Shunsuke Chiba

^*Corresponding author for this work

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

110 Citations (Scopus)

Abstract

A method for the synthesis of highly substituted pyri-dines from ,-unsaturated oximes and internal alkynes has been developed using [Cp*RhCl₂]₂-CsOPiv as the catalyst system. The present transformation is carried out by a redox-neutral sequence of vinylic C-H rhodation, alkyne insertion, and C-N bond formation of the putative vinyl rhodium intermediate with the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

Original language	English
Article number	B16911ST
Pages (from-to)	2789-2794
Number of pages	6
Journal	Synlett
Issue number	19
DOIs	https://doi.org/10.1055/s-0031-1289556
Publication status	Published - 2011
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

alkynes
C-H activation
oximes
pyridines
rhodium

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10.1055/s-0031-1289556

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title = "Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes",

abstract = "A method for the synthesis of highly substituted pyri-dines from ,-unsaturated oximes and internal alkynes has been developed using [Cp*RhCl2]2-CsOPiv as the catalyst system. The present transformation is carried out by a redox-neutral sequence of vinylic C-H rhodation, alkyne insertion, and C-N bond formation of the putative vinyl rhodium intermediate with the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.",

keywords = "alkynes, C-H activation, oximes, pyridines, rhodium",

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language = "English",

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T1 - Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes

AU - Too, Pei Chui

AU - Noji, Toshiharu

AU - Lim, Ying Jie

AU - Li, Xingwei

AU - Chiba, Shunsuke

PY - 2011

Y1 - 2011

N2 - A method for the synthesis of highly substituted pyri-dines from ,-unsaturated oximes and internal alkynes has been developed using [Cp*RhCl2]2-CsOPiv as the catalyst system. The present transformation is carried out by a redox-neutral sequence of vinylic C-H rhodation, alkyne insertion, and C-N bond formation of the putative vinyl rhodium intermediate with the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

AB - A method for the synthesis of highly substituted pyri-dines from ,-unsaturated oximes and internal alkynes has been developed using [Cp*RhCl2]2-CsOPiv as the catalyst system. The present transformation is carried out by a redox-neutral sequence of vinylic C-H rhodation, alkyne insertion, and C-N bond formation of the putative vinyl rhodium intermediate with the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

KW - alkynes

KW - C-H activation

KW - oximes

KW - pyridines

KW - rhodium

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SP - 2789

EP - 2794

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JF - Synlett

IS - 19

M1 - B16911ST

ER -

Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes

Abstract

ASJC Scopus Subject Areas

Keywords

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