Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts

Pei Chui Too; Sze Hui Chua; Siong Heng Wong; Shunsuke Chiba

doi:10.1021/jo200897q

Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts

Pei Chui Too, Sze Hui Chua, Siong Heng Wong, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

228 Citations (Scopus)

Abstract

A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc) ₂- [Cp*RhCl ₂] ₂ bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.

Original language	English
Pages (from-to)	6159-6168
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	76
Issue number	15
DOIs	https://doi.org/10.1021/jo200897q
Publication status	Published - Aug 5 2011
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

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title = "Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts",

abstract = "A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc) 2- [Cp*RhCl 2] 2 bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.",

author = "Too, {Pei Chui} and Chua, {Sze Hui} and Wong, {Siong Heng} and Shunsuke Chiba",

year = "2011",

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doi = "10.1021/jo200897q",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts

AU - Too, Pei Chui

AU - Chua, Sze Hui

AU - Wong, Siong Heng

AU - Chiba, Shunsuke

PY - 2011/8/5

Y1 - 2011/8/5

N2 - A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc) 2- [Cp*RhCl 2] 2 bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.

AB - A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc) 2- [Cp*RhCl 2] 2 bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.

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Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts

Abstract

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