GaCl3-catalyzed α-ethenylation reaction of ketone

Ryo Amemiya; Yoshio Nishimura; Masahiko Yamaguchi

doi:10.1055/s-2004-822363

GaCl₃-catalyzed α-ethenylation reaction of ketone

Ryo Amemiya, Yoshio Nishimura, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

20 Citations (Scopus)

Abstract

In the presence of catalytic amounts of GaCl₃ (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180°C. The roles of the base are to inhibit decomposition of the products and to promote proto-degallation of the organogallium intermediates.

Original language	English
Pages (from-to)	1307-1314
Number of pages	8
Journal	Synthesis
Issue number	9
DOIs	https://doi.org/10.1055/s-2004-822363
Publication status	Published - 2004 Jun 18

Keywords

Catalytic reaction
Cyclic ketone
GaCl
Silylethyne
α-ethenylation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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abstract = "In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180°C. The roles of the base are to inhibit decomposition of the products and to promote proto-degallation of the organogallium intermediates.",

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AU - Amemiya, Ryo

AU - Nishimura, Yoshio

AU - Yamaguchi, Masahiko

PY - 2004/6/18

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N2 - In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180°C. The roles of the base are to inhibit decomposition of the products and to promote proto-degallation of the organogallium intermediates.

AB - In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180°C. The roles of the base are to inhibit decomposition of the products and to promote proto-degallation of the organogallium intermediates.

KW - Catalytic reaction

KW - Cyclic ketone

KW - GaCl

KW - Silylethyne

KW - α-ethenylation

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JF - Synthesis

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