β-Silylethenylation of phenol with silylethyne using gallium trichloride

Katsumi Kobayashi; Mieko Arisawa; Masahiko Yamaguchi

doi:10.1016/S0020-1693(99)00325-4

β-Silylethenylation of phenol with silylethyne using gallium trichloride

Katsumi Kobayashi, Mieko Arisawa, Masahiko Yamaguchi

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

12 Citations (Scopus)

Abstract

Treatment of lithium phenoxide with silylethyne in the presence of GaCl₃ gives o-(β-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction.

Original language	English
Pages (from-to)	67-71
Number of pages	5
Journal	Inorganica Chimica Acta
Volume	296
Issue number	1
DOIs	https://doi.org/10.1016/S0020-1693(99)00325-4
Publication status	Published - 1999 Dec 15
Externally published	Yes

Keywords

Carbogallation
Carbometallation
Gallium trichloride
Phenol
β-Silylethenylation

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0020-1693(99)00325-4

Cite this

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title = "β-Silylethenylation of phenol with silylethyne using gallium trichloride",

abstract = "Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o-(β-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction.",

keywords = "Carbogallation, Carbometallation, Gallium trichloride, Phenol, β-Silylethenylation",

author = "Katsumi Kobayashi and Mieko Arisawa and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by grants from the Japan Society of Promotion of Science (RFTF 97P00302) and the Ministry of Education, Science and Culture, Japan (No. 08404050). M.A. expresses her thanks to JSPS for a Grant-in-Aid for encouragement of Young Scientists No. 1177 1374.",

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doi = "10.1016/S0020-1693(99)00325-4",

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journal = "Inorganica Chimica Acta",

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TY - JOUR

T1 - β-Silylethenylation of phenol with silylethyne using gallium trichloride

AU - Kobayashi, Katsumi

AU - Arisawa, Mieko

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by grants from the Japan Society of Promotion of Science (RFTF 97P00302) and the Ministry of Education, Science and Culture, Japan (No. 08404050). M.A. expresses her thanks to JSPS for a Grant-in-Aid for encouragement of Young Scientists No. 1177 1374.

PY - 1999/12/15

Y1 - 1999/12/15

N2 - Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o-(β-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction.

AB - Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o-(β-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction.

KW - Carbogallation

KW - Carbometallation

KW - Gallium trichloride

KW - Phenol

KW - β-Silylethenylation

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DO - 10.1016/S0020-1693(99)00325-4

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EP - 71

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

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ER -

β-Silylethenylation of phenol with silylethyne using gallium trichloride

Abstract

Keywords

ASJC Scopus subject areas

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