Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes

Pei Chui Too; Yi Feng Wang; Shunsuke Chiba

doi:10.1021/ol102504b

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes

Pei Chui Too, Yi Feng Wang, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

402 Citations (Scopus)

Abstract

A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl ₂]₂ - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on 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
Pages (from-to)	5688-5691
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	24
DOIs	https://doi.org/10.1021/ol102504b
Publication status	Published - Dec 17 2010
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102504b

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abstract = "A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl 2]2 - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N - O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.",

author = "Too, {Pei Chui} and Wang, {Yi Feng} and Shunsuke Chiba",

year = "2010",

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AU - Too, Pei Chui

AU - Wang, Yi Feng

AU - Chiba, Shunsuke

PY - 2010/12/17

Y1 - 2010/12/17

N2 - A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl 2]2 - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N - O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

AB - A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl 2]2 - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N - O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

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JO - Organic Letters

JF - Organic Letters

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Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes

Abstract

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