Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO                         2                          and H                         2

Zhengang Ke; Zhenzhen Yang; Zhenghui Liu; Bo Yu; Yanfei Zhao; Shien Guo; Yunyan Wu; Zhimin Liu

doi:10.1021/acs.orglett.8b02384

Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂

Zhengang Ke, Zhenzhen Yang, Zhenghui Liu, Bo Yu, Yanfei Zhao, Shien Guo, Yunyan Wu, Zhimin Liu

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

20 Scopus citations

Abstract

Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO ₂ /H ₂ over a cobalt-based catalytic system composed of CoF ₂ , P(CH ₂ CH ₂ PPh ₂ ) ₃ and K ₂ CO ₃ . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO ₂ hydrogenation, resulting in the formation of NNFA finally.

Original language	English
Pages (from-to)	6622-6626
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.8b02384
State	Published - Nov 2 2018
Externally published	Yes

Funding

This work was financially supported by the National Natural Science Foundation of China (Grant No. 21533011), and Chinese Academy of Sciences (Grant No. QYZDY-SSW-SLH013).

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10.1021/acs.orglett.8b02384

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Ke, Z., Yang, Z., Liu, Z., Yu, B., Zhao, Y., Guo, S., Wu, Y., & Liu, Z. (2018). Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ Organic Letters, 20(21), 6622-6626. https://doi.org/10.1021/acs.orglett.8b02384

Ke, Zhengang ; Yang, Zhenzhen ; Liu, Zhenghui et al. / Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ In: Organic Letters. 2018 ; Vol. 20, No. 21. pp. 6622-6626.

@article{cfc8aa7e19e8429f9bf7c74d0c670525,

title = " Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO 2 and H 2 ",

abstract = " Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO 2 /H 2 over a cobalt-based catalytic system composed of CoF 2 , P(CH 2 CH 2 PPh 2 ) 3 and K 2 CO 3 . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO 2 hydrogenation, resulting in the formation of NNFA finally.",

author = "Zhengang Ke and Zhenzhen Yang and Zhenghui Liu and Bo Yu and Yanfei Zhao and Shien Guo and Yunyan Wu and Zhimin Liu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = nov,

day = "2",

doi = "10.1021/acs.orglett.8b02384",

language = "English",

volume = "20",

pages = "6622--6626",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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}

Ke, Z, Yang, Z, Liu, Z, Yu, B, Zhao, Y, Guo, S, Wu, Y & Liu, Z 2018, ' Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ ', Organic Letters, vol. 20, no. 21, pp. 6622-6626. https://doi.org/10.1021/acs.orglett.8b02384

Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ . / Ke, Zhengang; Yang, Zhenzhen; Liu, Zhenghui et al.
In: Organic Letters, Vol. 20, No. 21, 02.11.2018, p. 6622-6626.

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

TY - JOUR

T1 - Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO 2 and H 2

AU - Ke, Zhengang

AU - Yang, Zhenzhen

AU - Liu, Zhenghui

AU - Yu, Bo

AU - Zhao, Yanfei

AU - Guo, Shien

AU - Wu, Yunyan

AU - Liu, Zhimin

PY - 2018/11/2

Y1 - 2018/11/2

N2 - Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO 2 /H 2 over a cobalt-based catalytic system composed of CoF 2 , P(CH 2 CH 2 PPh 2 ) 3 and K 2 CO 3 . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO 2 hydrogenation, resulting in the formation of NNFA finally.

AB - Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO 2 /H 2 over a cobalt-based catalytic system composed of CoF 2 , P(CH 2 CH 2 PPh 2 ) 3 and K 2 CO 3 . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO 2 hydrogenation, resulting in the formation of NNFA finally.

UR - https://www.scopus.com/pages/publications/85055900063

U2 - 10.1021/acs.orglett.8b02384

DO - 10.1021/acs.orglett.8b02384

M3 - Article

C2 - 30346788

AN - SCOPUS:85055900063

SN - 1523-7060

VL - 20

SP - 6622

EP - 6626

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Ke Z, Yang Z, Liu Z, Yu B, Zhao Y, Guo S et al. Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ Organic Letters. 2018 Nov 2;20(21):6622-6626. doi: 10.1021/acs.orglett.8b02384

Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂

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