Cobalt-Catalyzed Synthesis of Unsymmetrically N,N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO2 and H2

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 CO₂ and H₂

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

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

22 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 CO₂/H₂ over a cobalt-based catalytic system composed of CoF₂, P(CH₂CH₂PPh₂)₃ and K₂CO₃. 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 CO₂ 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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title = "Cobalt-Catalyzed Synthesis of Unsymmetrically N,N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO2 and H2",

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 CO2/H2 over a cobalt-based catalytic system composed of CoF2, P(CH2CH2PPh2)3 and K2CO3. 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 CO2 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: 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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TY - JOUR

T1 - Cobalt-Catalyzed Synthesis of Unsymmetrically N,N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO2 and H2

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 CO2/H2 over a cobalt-based catalytic system composed of CoF2, P(CH2CH2PPh2)3 and K2CO3. 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 CO2 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 CO2/H2 over a cobalt-based catalytic system composed of CoF2, P(CH2CH2PPh2)3 and K2CO3. 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 CO2 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 - Letter

C2 - 30346788

AN - SCOPUS:85055900063

SN - 1523-7060

VL - 20

SP - 6622

EP - 6626

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Cobalt-Catalyzed Synthesis of Unsymmetrically N,N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO₂ and H₂

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