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

Access to Document

10.1055/s-2004-822363

Cite this

@article{38944d65b4944a8685db9161cc0baab1,

title = "GaCl3-catalyzed α-ethenylation reaction of ketone",

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.",

keywords = "Catalytic reaction, Cyclic ketone, GaCl, Silylethyne, α-ethenylation",

author = "Ryo Amemiya and Yoshio Nishimura and Masahiko Yamaguchi",

year = "2004",

month = jun,

day = "18",

doi = "10.1055/s-2004-822363",

language = "English",

pages = "1307--1314",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "9",

}

TY - JOUR

T1 - GaCl3-catalyzed α-ethenylation reaction of ketone

AU - Amemiya, Ryo

AU - Nishimura, Yoshio

AU - Yamaguchi, Masahiko

PY - 2004/6/18

Y1 - 2004/6/18

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

UR - http://www.scopus.com/inward/record.url?scp=3042714333&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=3042714333&partnerID=8YFLogxK

U2 - 10.1055/s-2004-822363

DO - 10.1055/s-2004-822363

M3 - Article

AN - SCOPUS:3042714333

SP - 1307

EP - 1314

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 9

ER -