Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

Isao Kadota; Leopold Mpaka Lutete; Akinori Shibuya; Yoshinori Yamamoto

doi:10.1016/S0040-4039(01)01207-2

Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

Isao Kadota, Leopold Mpaka Lutete, Akinori Shibuya, Yoshinori Yamamoto

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

99 Citations (Scopus)

Abstract

The reaction of the internal alkyne 1 with alcohols 2 in the presence of a catalytic amount of Pd(PPh₃)₄ and benzoic acid in dioxane at 100°C gave the allylic ethers 3 in good to high yields. The reaction proceeds via the palladium/benzoic acid-catalyzed isomerization of the alkyne 1 to allene 6, followed by the addition of alcohols 2 to the π-allylpalladium intermediate 7 formed by the hydropalladation of the resulting allene 6. Furthermore, the intramolecular reaction of alkynes having a hydroxy group at the terminus of the carbon chain gave five- and six-membered cyclic ethers in good yields.

Original language	English
Pages (from-to)	6207-6210
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(01)01207-2
Publication status	Published - Aug 27 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01207-2

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title = "Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes",

abstract = "The reaction of the internal alkyne 1 with alcohols 2 in the presence of a catalytic amount of Pd(PPh3)4 and benzoic acid in dioxane at 100°C gave the allylic ethers 3 in good to high yields. The reaction proceeds via the palladium/benzoic acid-catalyzed isomerization of the alkyne 1 to allene 6, followed by the addition of alcohols 2 to the π-allylpalladium intermediate 7 formed by the hydropalladation of the resulting allene 6. Furthermore, the intramolecular reaction of alkynes having a hydroxy group at the terminus of the carbon chain gave five- and six-membered cyclic ethers in good yields.",

author = "Isao Kadota and Lutete, {Leopold Mpaka} and Akinori Shibuya and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan. ",

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T1 - Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

AU - Kadota, Isao

AU - Lutete, Leopold Mpaka

AU - Shibuya, Akinori

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan.

PY - 2001/8/27

Y1 - 2001/8/27

N2 - The reaction of the internal alkyne 1 with alcohols 2 in the presence of a catalytic amount of Pd(PPh3)4 and benzoic acid in dioxane at 100°C gave the allylic ethers 3 in good to high yields. The reaction proceeds via the palladium/benzoic acid-catalyzed isomerization of the alkyne 1 to allene 6, followed by the addition of alcohols 2 to the π-allylpalladium intermediate 7 formed by the hydropalladation of the resulting allene 6. Furthermore, the intramolecular reaction of alkynes having a hydroxy group at the terminus of the carbon chain gave five- and six-membered cyclic ethers in good yields.

AB - The reaction of the internal alkyne 1 with alcohols 2 in the presence of a catalytic amount of Pd(PPh3)4 and benzoic acid in dioxane at 100°C gave the allylic ethers 3 in good to high yields. The reaction proceeds via the palladium/benzoic acid-catalyzed isomerization of the alkyne 1 to allene 6, followed by the addition of alcohols 2 to the π-allylpalladium intermediate 7 formed by the hydropalladation of the resulting allene 6. Furthermore, the intramolecular reaction of alkynes having a hydroxy group at the terminus of the carbon chain gave five- and six-membered cyclic ethers in good yields.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

Abstract

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