Mixed phosphane η5-CpRuCl(PR3)2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes

Florian Boeck; Thomas Kribber; Li Xiao; Lukas Hintermann

doi:10.1021/ja2026823

Mixed phosphane η⁵-CpRuCl(PR₃)₂ complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes

Florian Boeck
, Thomas Kribber
, Li Xiao
, Lukas Hintermann

Associate Professorship of Catalytic Organic Synthesis

Technical University of Munich

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

84 Scopus citations

Abstract

The catalytic activity of [CpRu(L)₂(MeCN)]PF₆ (L = 2-diphenylphosphinopyridine with bulky groups at C-6) for anti-Markovnikov hydration of terminal alkynes to aldehydes is retained when one heterocyclic ligand L is replaced by L′ = PPh₃. Equal amounts of CpRuCl(PPh₃)₂ (1) and phosphane L in acetone solution equilibrate to a mixture of 1, CpRuCl(L)(PPh₃) (2), and CpRuCl(L)₂ (3), which acts as highly active in situ catalyst for preparative anti-Markovnikov hydration of alkynes in water-rich media (2 mol % [Ru], 60 °C, 3-18 h in 4:1 (v/v) acetone/water). Reactions were completed in <15 min at 160 °C.

Original language	English
Pages (from-to)	8138-8141
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	21
DOIs	https://doi.org/10.1021/ja2026823
State	Published - 1 Jun 2011

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title = "Mixed phosphane η5-CpRuCl(PR3)2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes",

abstract = "The catalytic activity of [CpRu(L)2(MeCN)]PF6 (L = 2-diphenylphosphinopyridine with bulky groups at C-6) for anti-Markovnikov hydration of terminal alkynes to aldehydes is retained when one heterocyclic ligand L is replaced by L′ = PPh3. Equal amounts of CpRuCl(PPh3)2 (1) and phosphane L in acetone solution equilibrate to a mixture of 1, CpRuCl(L)(PPh3) (2), and CpRuCl(L)2 (3), which acts as highly active in situ catalyst for preparative anti-Markovnikov hydration of alkynes in water-rich media (2 mol \% [Ru], 60 °C, 3-18 h in 4:1 (v/v) acetone/water). Reactions were completed in <15 min at 160 °C.",

author = "Florian Boeck and Thomas Kribber and Li Xiao and Lukas Hintermann",

year = "2011",

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doi = "10.1021/ja2026823",

language = "English",

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T1 - Mixed phosphane η5-CpRuCl(PR3)2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes

AU - Boeck, Florian

AU - Kribber, Thomas

AU - Xiao, Li

AU - Hintermann, Lukas

PY - 2011/6/1

Y1 - 2011/6/1

N2 - The catalytic activity of [CpRu(L)2(MeCN)]PF6 (L = 2-diphenylphosphinopyridine with bulky groups at C-6) for anti-Markovnikov hydration of terminal alkynes to aldehydes is retained when one heterocyclic ligand L is replaced by L′ = PPh3. Equal amounts of CpRuCl(PPh3)2 (1) and phosphane L in acetone solution equilibrate to a mixture of 1, CpRuCl(L)(PPh3) (2), and CpRuCl(L)2 (3), which acts as highly active in situ catalyst for preparative anti-Markovnikov hydration of alkynes in water-rich media (2 mol % [Ru], 60 °C, 3-18 h in 4:1 (v/v) acetone/water). Reactions were completed in <15 min at 160 °C.

AB - The catalytic activity of [CpRu(L)2(MeCN)]PF6 (L = 2-diphenylphosphinopyridine with bulky groups at C-6) for anti-Markovnikov hydration of terminal alkynes to aldehydes is retained when one heterocyclic ligand L is replaced by L′ = PPh3. Equal amounts of CpRuCl(PPh3)2 (1) and phosphane L in acetone solution equilibrate to a mixture of 1, CpRuCl(L)(PPh3) (2), and CpRuCl(L)2 (3), which acts as highly active in situ catalyst for preparative anti-Markovnikov hydration of alkynes in water-rich media (2 mol % [Ru], 60 °C, 3-18 h in 4:1 (v/v) acetone/water). Reactions were completed in <15 min at 160 °C.

UR - https://www.scopus.com/pages/publications/79957720795

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DO - 10.1021/ja2026823

M3 - Article

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SN - 0002-7863

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 21

ER -

Mixed phosphane η⁵-CpRuCl(PR₃)₂ complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes

Abstract

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