Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

Sergey Tin; Tamara Fanjul; Matthew L. Clarke

doi:10.3762/bjoc.11.70

Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

Sergey Tin, Tamara Fanjul, Matthew L. Clarke^*

^*Corresponding author for this work

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

Abstract

In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction.

Original language	English
Pages (from-to)	622-627
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.70
Publication status	Published - 5 May 2015

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

SDG 7 Affordable and Clean Energy

Keywords

Alkenes
Homogeneous catalysis
Hydrogenation
Renewable solvents
Tertiary amines
Asymmetric hydrogenation
Enantioselective synthesis
Functionalized enamines
Hydroformylation
Chemistry
Aldehydes
Ligands

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10.3762/bjoc.11.70

Tin_2015_Beilstein_Hydrogenation_CC
© 2015 Tin et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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@article{801740c1622f4b4496a151905d1a5c01,

title = "Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity",

abstract = "In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol \%) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction.",

keywords = "Alkenes, Homogeneous catalysis, Hydrogenation, Renewable solvents, Tertiary amines, Asymmetric hydrogenation, Enantioselective synthesis, Functionalized enamines, Hydroformylation, Chemistry, Aldehydes, Ligands",

author = "Sergey Tin and Tamara Fanjul and Clarke, \{Matthew L.\}",

note = "Date of Acceptance: 16/04/2015",

year = "2015",

month = may,

day = "5",

doi = "10.3762/bjoc.11.70",

language = "English",

volume = "11",

pages = "622--627",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Hydrogenation of unactivated enamines to tertiary amines

T2 - rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

AU - Tin, Sergey

AU - Fanjul, Tamara

AU - Clarke, Matthew L.

N1 - Date of Acceptance: 16/04/2015

PY - 2015/5/5

Y1 - 2015/5/5

N2 - In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction.

AB - In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction.

KW - Alkenes

KW - Homogeneous catalysis

KW - Hydrogenation

KW - Renewable solvents

KW - Tertiary amines

KW - Asymmetric hydrogenation

KW - Enantioselective synthesis

KW - Functionalized enamines

KW - Hydroformylation

KW - Chemistry

KW - Aldehydes

KW - Ligands

UR - http://www.beilstein-journals.org/bjoc/single/downloadSuppInfo.htm?publicId=1860-5397-11-70

UR - https://www.scopus.com/pages/publications/84930626192

U2 - 10.3762/bjoc.11.70

DO - 10.3762/bjoc.11.70

M3 - Article

SN - 1860-5397

VL - 11

SP - 622

EP - 627

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

Abstract

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Keywords

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