Efficient transformation of propargylic alcohols to α,β-unsaturated aldehydes catalyzed by ruthenium/water under neutral conditions

Toshiaki Suzuki; Makoto Tokunaga; Yasuo Wakatsuki

doi:10.1016/S0040-4039(02)01821-X

Efficient transformation of propargylic alcohols to α,β-unsaturated aldehydes catalyzed by ruthenium/water under neutral conditions

Toshiaki Suzuki, Makoto Tokunaga, Yasuo Wakatsuki

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

76 Citations (Scopus)

Abstract

α,β-Unsaturated aldehydes were selectively obtained in high yields from propargylic alcohols in aqueous solutions using RuCpCl(PR₃)₂ (Cp=η⁵-C₅H₅) as a catalyst. Of the tert-phosphine ligands examined, PMe₃ gave the most satisfactory results. Typically, RuCpCl(PMe₃)₂ (5 mol%) catalyzed the transformation of oct-1-yn-3-ol at 100°C to give 2-octenal in an isolated yield of 85% (E/Z=80/20).

Original language	English
Pages (from-to)	7531-7533
Number of pages	3
Journal	Tetrahedron Letters
Volume	43
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4039(02)01821-X
Publication status	Published - Oct 14 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)01821-X

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title = "Efficient transformation of propargylic alcohols to α,β-unsaturated aldehydes catalyzed by ruthenium/water under neutral conditions",

abstract = "α,β-Unsaturated aldehydes were selectively obtained in high yields from propargylic alcohols in aqueous solutions using RuCpCl(PR3)2 (Cp=η5-C5H5) as a catalyst. Of the tert-phosphine ligands examined, PMe3 gave the most satisfactory results. Typically, RuCpCl(PMe3)2 (5 mol%) catalyzed the transformation of oct-1-yn-3-ol at 100°C to give 2-octenal in an isolated yield of 85% (E/Z=80/20).",

author = "Toshiaki Suzuki and Makoto Tokunaga and Yasuo Wakatsuki",

year = "2002",

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doi = "10.1016/S0040-4039(02)01821-X",

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pages = "7531--7533",

journal = "Tetrahedron Letters",

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T1 - Efficient transformation of propargylic alcohols to α,β-unsaturated aldehydes catalyzed by ruthenium/water under neutral conditions

AU - Suzuki, Toshiaki

AU - Tokunaga, Makoto

AU - Wakatsuki, Yasuo

PY - 2002/10/14

Y1 - 2002/10/14

N2 - α,β-Unsaturated aldehydes were selectively obtained in high yields from propargylic alcohols in aqueous solutions using RuCpCl(PR3)2 (Cp=η5-C5H5) as a catalyst. Of the tert-phosphine ligands examined, PMe3 gave the most satisfactory results. Typically, RuCpCl(PMe3)2 (5 mol%) catalyzed the transformation of oct-1-yn-3-ol at 100°C to give 2-octenal in an isolated yield of 85% (E/Z=80/20).

AB - α,β-Unsaturated aldehydes were selectively obtained in high yields from propargylic alcohols in aqueous solutions using RuCpCl(PR3)2 (Cp=η5-C5H5) as a catalyst. Of the tert-phosphine ligands examined, PMe3 gave the most satisfactory results. Typically, RuCpCl(PMe3)2 (5 mol%) catalyzed the transformation of oct-1-yn-3-ol at 100°C to give 2-octenal in an isolated yield of 85% (E/Z=80/20).

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DO - 10.1016/S0040-4039(02)01821-X

M3 - Article

AN - SCOPUS:0037078485

SN - 0040-4039

VL - 43

SP - 7531

EP - 7533

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Efficient transformation of propargylic alcohols to α,β-unsaturated aldehydes catalyzed by ruthenium/water under neutral conditions

Abstract

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