Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

Xing Sheng; Jiayi Xian; Shuting Liu; Xiangyu Zhang; Bin Li; Jun Wang; Xiuwen Chen; Feng Xie

doi:10.1016/j.jcat.2023.03.019

Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

Xing Sheng, Jiayi Xian, Shuting Liu, Xiangyu Zhang, Bin Li^*, Jun Wang, Xiuwen Chen, Feng Xie^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

9 Citations (Scopus)

Abstract

Green palladium-catalyzed nitroarene/nitrile reductive cross-annulation chemistry that facilitates straightforward access to pyrrolo[1,2-a]quinoxaline derivatives is described herein. A range of nitriles are activated as carbon synthons to form intramolecular C-N and C-C bonds using this chemistry. The synthetic protocol has the advantages of broad substrate scope, excellent functional group tolerance, and the use of environment-friendly water and inexpensive HCOONa/HCOOH as the solvent and hydrogen donors, respectively. The catalyst is conveniently recycled by filtration and can be reused at least five times without obvious deactivation. This study offers an important platform for converting bulk chemical motifs into value-added functional frameworks.

Original language	English
Pages (from-to)	156-161
Number of pages	6
Journal	Journal of Catalysis
Volume	421
Early online date	15 Mar 2023
DOIs	https://doi.org/10.1016/j.jcat.2023.03.019
Publication status	Published - May 2023

User-Defined Keywords

Carbon synthons
Nitriles
Palladium
Pyrrolo[1,2-α]quinoxalines
Transfer hydrogenation

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10.1016/j.jcat.2023.03.019

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@article{9e42abd19ab34bf085be773a596b9766,

title = "Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons",

abstract = "Green palladium-catalyzed nitroarene/nitrile reductive cross-annulation chemistry that facilitates straightforward access to pyrrolo[1,2-a]quinoxaline derivatives is described herein. A range of nitriles are activated as carbon synthons to form intramolecular C-N and C-C bonds using this chemistry. The synthetic protocol has the advantages of broad substrate scope, excellent functional group tolerance, and the use of environment-friendly water and inexpensive HCOONa/HCOOH as the solvent and hydrogen donors, respectively. The catalyst is conveniently recycled by filtration and can be reused at least five times without obvious deactivation. This study offers an important platform for converting bulk chemical motifs into value-added functional frameworks.",

keywords = "Carbon synthons, Nitriles, Palladium, Pyrrolo[1,2-α]quinoxalines, Transfer hydrogenation",

author = "Xing Sheng and Jiayi Xian and Shuting Liu and Xiangyu Zhang and Bin Li and Jun Wang and Xiuwen Chen and Feng Xie",

note = "Funding Information: We thank the Department of Education of Guangdong province (2019KZDXM052, 2020KQNCX093, 2021ZDZX2045, 2022ZDZX2060), “Climbing Program” Special Funds of Guangdong Province (pdjh2021b0516), the Foundation of Wuyi University (2021WGALH06) and National Natural Science Foundation of China (22101212) for financial support. The authors thank Shiyanjia Lab (www.shiyanjia.com) for the support of ICP-OES test as well. Publisher Copyright: {\textcopyright} 2023 Elsevier Inc.",

year = "2023",

month = may,

doi = "10.1016/j.jcat.2023.03.019",

language = "English",

volume = "421",

pages = "156--161",

journal = "Journal of Catalysis",

issn = "0021-9517",

publisher = "Academic Press Inc.",

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TY - JOUR

T1 - Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

AU - Sheng, Xing

AU - Xian, Jiayi

AU - Liu, Shuting

AU - Zhang, Xiangyu

AU - Li, Bin

AU - Wang, Jun

AU - Chen, Xiuwen

AU - Xie, Feng

N1 - Funding Information: We thank the Department of Education of Guangdong province (2019KZDXM052, 2020KQNCX093, 2021ZDZX2045, 2022ZDZX2060), “Climbing Program” Special Funds of Guangdong Province (pdjh2021b0516), the Foundation of Wuyi University (2021WGALH06) and National Natural Science Foundation of China (22101212) for financial support. The authors thank Shiyanjia Lab (www.shiyanjia.com) for the support of ICP-OES test as well. Publisher Copyright: © 2023 Elsevier Inc.

PY - 2023/5

Y1 - 2023/5

N2 - Green palladium-catalyzed nitroarene/nitrile reductive cross-annulation chemistry that facilitates straightforward access to pyrrolo[1,2-a]quinoxaline derivatives is described herein. A range of nitriles are activated as carbon synthons to form intramolecular C-N and C-C bonds using this chemistry. The synthetic protocol has the advantages of broad substrate scope, excellent functional group tolerance, and the use of environment-friendly water and inexpensive HCOONa/HCOOH as the solvent and hydrogen donors, respectively. The catalyst is conveniently recycled by filtration and can be reused at least five times without obvious deactivation. This study offers an important platform for converting bulk chemical motifs into value-added functional frameworks.

AB - Green palladium-catalyzed nitroarene/nitrile reductive cross-annulation chemistry that facilitates straightforward access to pyrrolo[1,2-a]quinoxaline derivatives is described herein. A range of nitriles are activated as carbon synthons to form intramolecular C-N and C-C bonds using this chemistry. The synthetic protocol has the advantages of broad substrate scope, excellent functional group tolerance, and the use of environment-friendly water and inexpensive HCOONa/HCOOH as the solvent and hydrogen donors, respectively. The catalyst is conveniently recycled by filtration and can be reused at least five times without obvious deactivation. This study offers an important platform for converting bulk chemical motifs into value-added functional frameworks.

KW - Carbon synthons

KW - Nitriles

KW - Palladium

KW - Pyrrolo[1,2-α]quinoxalines

KW - Transfer hydrogenation

UR - http://www.scopus.com/inward/record.url?scp=85150275629&partnerID=8YFLogxK

U2 - 10.1016/j.jcat.2023.03.019

DO - 10.1016/j.jcat.2023.03.019

M3 - Journal article

SN - 0021-9517

VL - 421

SP - 156

EP - 161

JO - Journal of Catalysis

JF - Journal of Catalysis

ER -

Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons

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