Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

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

Research output: Contribution to journalArticle

89 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 languageEnglish
Pages (from-to)6207-6210
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number35
DOIs
Publication statusPublished - Aug 27 2001
Externally publishedYes

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Benzoic Acid
Alkynes
Palladium
Cyclic Ethers
Alcohols
Ethers
Isomerization
Carbon
propadiene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes. / Kadota, Isao; Lutete, Leopold Mpaka; Shibuya, Akinori; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 42, No. 35, 27.08.2001, p. 6207-6210.

Research output: Contribution to journalArticle

Kadota, Isao ; Lutete, Leopold Mpaka ; Shibuya, Akinori ; Yamamoto, Yoshinori. / Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 35. pp. 6207-6210.
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