Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes

Hung Wai Cheung; Chau Ming So; Kwok Hung Pun; Zhongyuan Zhou; Chak Po Lau

doi:10.1002/adsc.201000567

Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes

Hung Wai Cheung, Chau Ming So, Kwok Hung Pun, Zhongyuan Zhou, Chak Po Lau

Research output: Journal article publication › Journal article › Academic research › peer-review

36 Citations (Scopus)

Abstract

The hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex TpRu[4-CF3C6H4N(PPh2)2](OTf) (I) [Tp=hydro(trispyrazolyl)borate] catalyzes the Markovnikov addition of β-diketones to unactivated 1-alkynes in good to excellent yields. The reaction proceeds under solvent-free and additive-free conditions and the catalyst loading can be reduced down to 0.4amol%. Complex I (1amol%) also catalyzes the addition of secondary amines to aromatic terminal alkynes, unusual anti-Markovnikov products are exclusively formed. KGaA, Weinheim.

Original language	English
Pages (from-to)	411-425
Number of pages	15
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	2-3
DOIs	https://doi.org/10.1002/adsc.201000567
Publication status	Published - 11 Feb 2011

Keywords

β-diketones
1-alkynes
addition reaction
ruthenium
secondary amines

ASJC Scopus subject areas

Catalysis
Organic Chemistry

More information

10.1002/adsc.201000567

Cite this

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title = "Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes",

abstract = "The hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex TpRu[4-CF3C6H4N(PPh2)2](OTf) (I) [Tp=hydro(trispyrazolyl)borate] catalyzes the Markovnikov addition of β-diketones to unactivated 1-alkynes in good to excellent yields. The reaction proceeds under solvent-free and additive-free conditions and the catalyst loading can be reduced down to 0.4amol%. Complex I (1amol%) also catalyzes the addition of secondary amines to aromatic terminal alkynes, unusual anti-Markovnikov products are exclusively formed. KGaA, Weinheim.",

keywords = "β-diketones, 1-alkynes, addition reaction, ruthenium, secondary amines",

author = "Cheung, {Hung Wai} and So, {Chau Ming} and Pun, {Kwok Hung} and Zhongyuan Zhou and Lau, {Chak Po}",

year = "2011",

month = feb,

day = "11",

doi = "10.1002/adsc.201000567",

language = "English",

volume = "353",

pages = "411--425",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "2-3",

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Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes. / Cheung, Hung Wai; So, Chau Ming; Pun, Kwok Hung et al.
In: Advanced Synthesis and Catalysis, Vol. 353, No. 2-3, 11.02.2011, p. 411-425.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes

AU - Cheung, Hung Wai

AU - So, Chau Ming

AU - Pun, Kwok Hung

AU - Zhou, Zhongyuan

AU - Lau, Chak Po

PY - 2011/2/11

Y1 - 2011/2/11

N2 - The hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex TpRu[4-CF3C6H4N(PPh2)2](OTf) (I) [Tp=hydro(trispyrazolyl)borate] catalyzes the Markovnikov addition of β-diketones to unactivated 1-alkynes in good to excellent yields. The reaction proceeds under solvent-free and additive-free conditions and the catalyst loading can be reduced down to 0.4amol%. Complex I (1amol%) also catalyzes the addition of secondary amines to aromatic terminal alkynes, unusual anti-Markovnikov products are exclusively formed. KGaA, Weinheim.

AB - The hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex TpRu[4-CF3C6H4N(PPh2)2](OTf) (I) [Tp=hydro(trispyrazolyl)borate] catalyzes the Markovnikov addition of β-diketones to unactivated 1-alkynes in good to excellent yields. The reaction proceeds under solvent-free and additive-free conditions and the catalyst loading can be reduced down to 0.4amol%. Complex I (1amol%) also catalyzes the addition of secondary amines to aromatic terminal alkynes, unusual anti-Markovnikov products are exclusively formed. KGaA, Weinheim.

KW - β-diketones

KW - 1-alkynes

KW - addition reaction

KW - ruthenium

KW - secondary amines

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U2 - 10.1002/adsc.201000567

DO - 10.1002/adsc.201000567

M3 - Journal article

SN - 1615-4150

VL - 353

SP - 411

EP - 425

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 2-3

ER -

Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes

Abstract

Keywords

ASJC Scopus subject areas

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