Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines

Huaifeng Li; Abdullah Al Dakhil; Daniel Lupp; Sandeep Suryabhan Gholap; Zhiping Lai; Lan-Chang Liang; Kuo-Wei Huang

doi:10.1021/acs.orglett.8b02744

Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines

Huaifeng Li, Abdullah Al Dakhil, Daniel Lupp, Sandeep Suryabhan Gholap, Zhiping Lai, Lan-Chang Liang, Kuo-Wei Huang

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

42 Scopus citations

Abstract

The first example of cobalt-catalyzed selective hydrogenation of nitriles to secondary imines is reported. The results demonstrate the significantly different selectivity compared with the previously reported cobalt catalytic system during the nitrile hydrogenation. A variety of aromatic and aliphatic nitriles are hydrogenated to the corresponding secondary imines.

Original language	English (US)
Pages (from-to)	6430-6435
Number of pages	6
Journal	Organic Letters
Volume	20
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.8b02744
State	Published - Oct 2018

Bibliographical note

KAUST Repository Item: Exported on 2021-01-19
Acknowledgements: Financial support was provided by King Abdullah University of Science and Technology (KAUST) and the Ministry of Science and Technology of Taiwan (MOST 106-2113-M-110-003).

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10.1021/acs.orglett.8b02744

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title = "Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines",

abstract = "The first example of cobalt-catalyzed selective hydrogenation of nitriles to secondary imines is reported. The results demonstrate the significantly different selectivity compared with the previously reported cobalt catalytic system during the nitrile hydrogenation. A variety of aromatic and aliphatic nitriles are hydrogenated to the corresponding secondary imines.",

author = "Huaifeng Li and {Al Dakhil}, Abdullah and Daniel Lupp and Gholap, {Sandeep Suryabhan} and Zhiping Lai and Lan-Chang Liang and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2021-01-19 Acknowledgements: Financial support was provided by King Abdullah University of Science and Technology (KAUST) and the Ministry of Science and Technology of Taiwan (MOST 106-2113-M-110-003).",

year = "2018",

month = oct,

doi = "10.1021/acs.orglett.8b02744",

language = "English (US)",

volume = "20",

pages = "6430--6435",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines

AU - Li, Huaifeng

AU - Al Dakhil, Abdullah

AU - Lupp, Daniel

AU - Gholap, Sandeep Suryabhan

AU - Lai, Zhiping

AU - Liang, Lan-Chang

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2021-01-19 Acknowledgements: Financial support was provided by King Abdullah University of Science and Technology (KAUST) and the Ministry of Science and Technology of Taiwan (MOST 106-2113-M-110-003).

PY - 2018/10

Y1 - 2018/10

N2 - The first example of cobalt-catalyzed selective hydrogenation of nitriles to secondary imines is reported. The results demonstrate the significantly different selectivity compared with the previously reported cobalt catalytic system during the nitrile hydrogenation. A variety of aromatic and aliphatic nitriles are hydrogenated to the corresponding secondary imines.

AB - The first example of cobalt-catalyzed selective hydrogenation of nitriles to secondary imines is reported. The results demonstrate the significantly different selectivity compared with the previously reported cobalt catalytic system during the nitrile hydrogenation. A variety of aromatic and aliphatic nitriles are hydrogenated to the corresponding secondary imines.

UR - http://hdl.handle.net/10754/630573

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.8b02744

UR - http://www.scopus.com/inward/record.url?scp=85054363733&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02744

DO - 10.1021/acs.orglett.8b02744

M3 - Article

C2 - 30272984

AN - SCOPUS:85054363733

SN - 1523-7060

VL - 20

SP - 6430

EP - 6435

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines

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CCDC 1858908: Experimental Crystal Structure Determination : chloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-di-t-butyl(phosphinous amide)])-cobalt chloride methanol solvate

CCDC 1859265: Experimental Crystal Structure Determination : dichloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-dicyclopentyl(phosphinous amide)])-cobalt

CCDC 1858909: Experimental Crystal Structure Determination : dichloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-diisopropyl(phosphinous amide)])-cobalt tetrahydrofuran solvate

Cite this

Cobalt-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines

Abstract

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Datasets

CCDC 1858908: Experimental Crystal Structure Determination : chloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-di-t-butyl(phosphinous amide)])-cobalt chloride methanol solvate

CCDC 1859265: Experimental Crystal Structure Determination : dichloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-dicyclopentyl(phosphinous amide)])-cobalt

CCDC 1858909: Experimental Crystal Structure Determination : dichloro-(N,N'-(pyridine-2,6-diyl)bis[P,P-diisopropyl(phosphinous amide)])-cobalt tetrahydrofuran solvate

Cite this