Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

Toshiaki Suzuki; Makoto Tokunaga; Yasuo Wakatsuki

doi:10.1021/ol0003937

Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

Toshiaki Suzuki, Makoto Tokunaga, Yasuo Wakatsuki

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

159 Citations (Scopus)

Abstract

Highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphme ligands. Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100°C to give hexanal in 95% yield: 2-hexanone is not detected at all.

Original language	English
Pages (from-to)	735-736
Number of pages	2
Journal	Organic Letters
Volume	3
Issue number	5
DOIs	https://doi.org/10.1021/ol0003937
Publication status	Published - Mar 8 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0003937

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abstract = "Highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphme ligands. Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100°C to give hexanal in 95% yield: 2-hexanone is not detected at all.",

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

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AU - Wakatsuki, Yasuo

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N2 - Highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphme ligands. Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100°C to give hexanal in 95% yield: 2-hexanone is not detected at all.

AB - Highly regioselective, efficient, and substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphme ligands. Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100°C to give hexanal in 95% yield: 2-hexanone is not detected at all.

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Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

Abstract

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