Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction

Takashi Ooi; Kohsuke Ohmatsu; Kouji Sasaki; Tomoya Miura; Keiji Maruoka

doi:10.1016/S0040-4039(03)00472-6

Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction

Takashi Ooi, Kohsuke Ohmatsu, Kouji Sasaki, Tomoya Miura, Keiji Maruoka

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

32 Citations (Scopus)

Abstract

Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide (3) has been evaluated as an aluminum-based catalyst for the Tishchenko reaction. Compound 3 was found to exert high catalytic activity in the reaction with aliphatic aldehydes and also enabled smooth dimerization of enolizable aldehydes. This advantage was highlighted by the quantitative formation of ethyl acetate from acetaldehyde by the present system.

Original language	English
Pages (from-to)	3191-3193
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(03)00472-6
Publication status	Published - Apr 7 2003
Externally published	Yes

Keywords

Aldehydes
Aluminum alkoxide
Carboxylic esters
Tishchenko reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)00472-6

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title = "Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction",

abstract = "Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide (3) has been evaluated as an aluminum-based catalyst for the Tishchenko reaction. Compound 3 was found to exert high catalytic activity in the reaction with aliphatic aldehydes and also enabled smooth dimerization of enolizable aldehydes. This advantage was highlighted by the quantitative formation of ethyl acetate from acetaldehyde by the present system.",

keywords = "Aldehydes, Aluminum alkoxide, Carboxylic esters, Tishchenko reaction",

author = "Takashi Ooi and Kohsuke Ohmatsu and Kouji Sasaki and Tomoya Miura and Keiji Maruoka",

note = "Funding Information: We gratefully appreciate Messrs. Tetsuo Nakajo and Yasushi Kuroda (SHOWA DENKO K. K. Corporate R&D Center) for providing valuable information. This work was partially supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. T.M. thanks the Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists.",

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doi = "10.1016/S0040-4039(03)00472-6",

language = "English",

volume = "44",

pages = "3191--3193",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "15",

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T1 - Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction

AU - Ooi, Takashi

AU - Ohmatsu, Kohsuke

AU - Sasaki, Kouji

AU - Miura, Tomoya

AU - Maruoka, Keiji

N1 - Funding Information: We gratefully appreciate Messrs. Tetsuo Nakajo and Yasushi Kuroda (SHOWA DENKO K. K. Corporate R&D Center) for providing valuable information. This work was partially supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. T.M. thanks the Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists.

PY - 2003/4/7

Y1 - 2003/4/7

N2 - Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide (3) has been evaluated as an aluminum-based catalyst for the Tishchenko reaction. Compound 3 was found to exert high catalytic activity in the reaction with aliphatic aldehydes and also enabled smooth dimerization of enolizable aldehydes. This advantage was highlighted by the quantitative formation of ethyl acetate from acetaldehyde by the present system.

AB - Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide (3) has been evaluated as an aluminum-based catalyst for the Tishchenko reaction. Compound 3 was found to exert high catalytic activity in the reaction with aliphatic aldehydes and also enabled smooth dimerization of enolizable aldehydes. This advantage was highlighted by the quantitative formation of ethyl acetate from acetaldehyde by the present system.

KW - Aldehydes

KW - Aluminum alkoxide

KW - Carboxylic esters

KW - Tishchenko reaction

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U2 - 10.1016/S0040-4039(03)00472-6

DO - 10.1016/S0040-4039(03)00472-6

M3 - Article

AN - SCOPUS:0037424750

SN - 0040-4039

VL - 44

SP - 3191

EP - 3193

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction

Abstract

Keywords

ASJC Scopus subject areas

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