Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

Yoichiro Kuninobu; Hisatsugu Takata; Atsushi Kawata; Kazuhiko Takai

doi:10.1021/ol801226t

Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

Yoichiro Kuninobu, Hisatsugu Takata, Atsushi Kawata, Kazuhiko Takai

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

60 Citations (Scopus)

Abstract

(Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)₃(thf)] ₂, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

Original language	English
Pages (from-to)	3133-3135
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	14
DOIs	https://doi.org/10.1021/ol801226t
Publication status	Published - Dec 1 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage",

abstract = "(Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.",

author = "Yoichiro Kuninobu and Hisatsugu Takata and Atsushi Kawata and Kazuhiko Takai",

year = "2008",

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doi = "10.1021/ol801226t",

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journal = "Organic Letters",

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T1 - Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

AU - Kuninobu, Yoichiro

AU - Takata, Hisatsugu

AU - Kawata, Atsushi

AU - Takai, Kazuhiko

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

AB - (Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

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EP - 3135

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

Abstract

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