(R)-binap-mediated asymmetric hydrogenation with a rhodacarborane catalyst in ionic-liquid media

Zhu Yinghuai; Keith Carpenter; Ching Chi Bun; Stefan Bahnmueller; Chan Pek Ke; Venugopal Shanmugham Srid; Leong Weng Kee; M. Frederick Hawthorne

doi:10.1002/anie.200351273

(R)-binap-mediated asymmetric hydrogenation with a rhodacarborane catalyst in ionic-liquid media

Zhu Yinghuai^*, Keith Carpenter, Ching Chi Bun, Stefan Bahnmueller, Chan Pek Ke, Venugopal Shanmugham Srid, Leong Weng Kee, M. Frederick Hawthorne

^*Corresponding author for this work

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

63 Citations (Scopus)

Abstract

Unsymmetrical aryl ketones undergo asymmetric hydrogenation in ionic-liquid media in the presence of (R)-binap and a rhodacarborane catalyst derived from the suicide precursor 1 (see scheme). Ketones that are poor substrates for other methods can be hydrogenated in quantitative yields with very high enantioselectivities (97.3-99.5% ee). The novel ionic liquid (N-n-butylpyridinium)⁺(closo-CB₁₁H₁₂) ^- provides a superior medium for these reactions.

Original language	English
Pages (from-to)	3792-3795
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	32
DOIs	https://doi.org/10.1002/anie.200351273
Publication status	Published - Aug 18 2003
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

Asymmetric catalysis
Carboranes
Hydrogenation
Ionic liquids
P ligands
Rhodium

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.200351273

Cite this

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title = "(R)-binap-mediated asymmetric hydrogenation with a rhodacarborane catalyst in ionic-liquid media",

abstract = "Unsymmetrical aryl ketones undergo asymmetric hydrogenation in ionic-liquid media in the presence of (R)-binap and a rhodacarborane catalyst derived from the suicide precursor 1 (see scheme). Ketones that are poor substrates for other methods can be hydrogenated in quantitative yields with very high enantioselectivities (97.3-99.5% ee). The novel ionic liquid (N-n-butylpyridinium)+(closo-CB11H12) - provides a superior medium for these reactions.",

keywords = "Asymmetric catalysis, Carboranes, Hydrogenation, Ionic liquids, P ligands, Rhodium",

author = "Zhu Yinghuai and Keith Carpenter and Bun, {Ching Chi} and Stefan Bahnmueller and Ke, {Chan Pek} and Srid, {Venugopal Shanmugham} and Kee, {Leong Weng} and Hawthorne, {M. Frederick}",

year = "2003",

month = aug,

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doi = "10.1002/anie.200351273",

language = "English",

volume = "42",

pages = "3792--3795",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "32",

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TY - JOUR

T1 - (R)-binap-mediated asymmetric hydrogenation with a rhodacarborane catalyst in ionic-liquid media

AU - Yinghuai, Zhu

AU - Carpenter, Keith

AU - Bun, Ching Chi

AU - Bahnmueller, Stefan

AU - Ke, Chan Pek

AU - Srid, Venugopal Shanmugham

AU - Kee, Leong Weng

AU - Hawthorne, M. Frederick

PY - 2003/8/18

Y1 - 2003/8/18

N2 - Unsymmetrical aryl ketones undergo asymmetric hydrogenation in ionic-liquid media in the presence of (R)-binap and a rhodacarborane catalyst derived from the suicide precursor 1 (see scheme). Ketones that are poor substrates for other methods can be hydrogenated in quantitative yields with very high enantioselectivities (97.3-99.5% ee). The novel ionic liquid (N-n-butylpyridinium)+(closo-CB11H12) - provides a superior medium for these reactions.

AB - Unsymmetrical aryl ketones undergo asymmetric hydrogenation in ionic-liquid media in the presence of (R)-binap and a rhodacarborane catalyst derived from the suicide precursor 1 (see scheme). Ketones that are poor substrates for other methods can be hydrogenated in quantitative yields with very high enantioselectivities (97.3-99.5% ee). The novel ionic liquid (N-n-butylpyridinium)+(closo-CB11H12) - provides a superior medium for these reactions.

KW - Asymmetric catalysis

KW - Carboranes

KW - Hydrogenation

KW - Ionic liquids

KW - P ligands

KW - Rhodium

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U2 - 10.1002/anie.200351273

DO - 10.1002/anie.200351273

M3 - Article

AN - SCOPUS:0041363235

SN - 1433-7851

VL - 42

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EP - 3795

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

(R)-binap-mediated asymmetric hydrogenation with a rhodacarborane catalyst in ionic-liquid media

Abstract

ASJC Scopus Subject Areas

Keywords

UN SDGs

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