o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst

Naoki Asao; Atsushi Shibato; Yoshifumi Itagaki; Fabrice Jourdan; Keiji Maruoka

doi:10.1016/S0040-4039(98)00453-5

o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu₄NF catalyst

Naoki Asao, Atsushi Shibato, Yoshifumi Itagaki, Fabrice Jourdan, Keiji Maruoka

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

23 Citations (Scopus)

Abstract

A new type of fluoride ion catalyzed allylation agent, o- bis(allyldimethylsilyl)benzene (1a) and bis(allyldimethylsilyl)methane (1b), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to complex with Bu₄NF by the favorable chelation of bis(silane) toward the fluoride ion.

Original language	English
Pages (from-to)	3177-3180
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(98)00453-5
Publication status	Published - 1998 May 14
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst",

abstract = "A new type of fluoride ion catalyzed allylation agent, o- bis(allyldimethylsilyl)benzene (1a) and bis(allyldimethylsilyl)methane (1b), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to complex with Bu4NF by the favorable chelation of bis(silane) toward the fluoride ion.",

author = "Naoki Asao and Atsushi Shibato and Yoshifumi Itagaki and Fabrice Jourdan and Keiji Maruoka",

note = "Funding Information: Acknowledgment. This work was partially supported by the Asahi Glass Foundation, the Akiyama Foundation, the Ogasawara Foundation for the Promotion of Science and Engineering, and a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.",

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T1 - o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst

AU - Asao, Naoki

AU - Shibato, Atsushi

AU - Itagaki, Yoshifumi

AU - Jourdan, Fabrice

AU - Maruoka, Keiji

N1 - Funding Information: Acknowledgment. This work was partially supported by the Asahi Glass Foundation, the Akiyama Foundation, the Ogasawara Foundation for the Promotion of Science and Engineering, and a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.

PY - 1998/5/14

Y1 - 1998/5/14

N2 - A new type of fluoride ion catalyzed allylation agent, o- bis(allyldimethylsilyl)benzene (1a) and bis(allyldimethylsilyl)methane (1b), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to complex with Bu4NF by the favorable chelation of bis(silane) toward the fluoride ion.

AB - A new type of fluoride ion catalyzed allylation agent, o- bis(allyldimethylsilyl)benzene (1a) and bis(allyldimethylsilyl)methane (1b), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to complex with Bu4NF by the favorable chelation of bis(silane) toward the fluoride ion.

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o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu₄NF catalyst

Abstract

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