Green synthesis of benzimidazoles via the palladium catalyzed one-pot reductive coupling of nitroarylamines with nitriles

被引：0

作者：

Zhou, Kun ^{[1
]}

Sheng, Xing ^{[1
]}

Liu, Haibo ^{[1
]}

Ye, Zhi ^{[2
]}

Gao, Jingwen ^{[1
]}

Xie, Feng ^{[1
,3
]}

机构：

[1] Wuyi Univ, Sch Environm & Chem Engn, Jiangmen Key Lab Synthet Chem & Cleaner Prod, Jiangmen 529020, Guangdong, Peoples R China

[2] Carpoly Chem Grp Co Ltd, Guangdong Prov Key Lab Environm Friendly Coatings, Jiangmen 529020, Guangdong, Peoples R China

[3] Guangdong Lab Chem & Fine Chem Ind Jieyang Ctr, Jieyang 515200, Guangdong, Peoples R China

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2025年 / 1333卷

关键词：

Palladium; Nitriles; Benzimidazoles; Reductive coupling; Carbon synthons; EFFICIENT SYNTHESIS; DIVERSE; ACETYLATION; NITROARENES; CYCLIZATION; FACILE; LIGAND;

D O I：

10.1016/j.molstruc.2025.141747

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient catalytic protocol that uses a readily available Pd-based catalyst has been developed for the synthesis of multi-functionalized benzimidazoles. The selective one-pot reductive coupling reaction of nitriles with nitroarylamines is advantageous owing to its broad substrate scope and the use of environmentally friendly water and biomass-derived HCOOH as the solvent and hydrogen donor, respectively. In this transformation, various types of nitriles are activated in situ to form imines, which act as carbon synthons to participate in the formation of intramolecular C-N bonds. Furthermore, the catalyst is not obviously deactivated when reused at least six times. This research presents a significant platform for transforming simple chemical building blocks into more valuable and complex functional frameworks.

引用

页数：9

共 55 条

[1] A polymer-supported salen-palladium complex as a heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction [J].

Balinge, Kamlesh Rudreshwar ;

Bhagat, Pundlik Rambhau .

INORGANICA CHIMICA ACTA, 2019, 495

[2] Iron(III)-salen complex on a polymer scaffold as heterogeneous catalyst for synthesis of benzimidazoles [J].

Balinge, Kamlesh Rudreshwar ;

Datir, Sagar Krushnarao ;

Khajone, Vijay Baburao ;

Bhansali, Karan Jivanlal ;

Khiratkar, Avinash Ganesh ;

Bhagat, Pundlik Rambhau .

RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (02) :155-168

[3] Accelerated microdroplet synthesis of benzimidazoles by nucleophilic addition to protonated carboxylic acids [J].

Basuri, Pallab ;

Gonzalez, L. Edwin ;

Morato, Nicolas M. ;

Pradeep, Thalappil ;

Cooks, R. Graham .

CHEMICAL SCIENCE, 2020, 11 (47) :12686-12694

[4] Selective Synthesis of Imines by Photo-Oxidative Amine Cross-Condensation Catalyzed by PCN-222(Pd) [J].

Bermejo-Lopez, Aitor ;

Carrasco, Sergio ;

Tortajada, Pedro J. ;

Kopf, Kenji P. M. ;

Sanz-Marco, Amparo ;

Hvid, Mathias S. ;

Lock, Nina ;

Martin-Matute, Belen .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2021, 9 (43) :14405-14415

[5] Improved and ligand-free copper-catalyzed cyclization for an efficient synthesis of benzimidazoles from o-bromoarylamine and nitriles [J].

Bonku, Emmanuel Mintah ;

Qin, Hongjian ;

Odilov, Abdullajon ;

Abduahadi, Safomuddin ;

Guma, Samuel Desta ;

Yang, Feipu ;

Zhu, Fuqiang ;

Aisa, Haji A. ;

Shen, Jingshan .

RSC ADVANCES, 2024, 14 (10) :6906-6916

[6] Recent trends for chemoselectivity modulation in one-pot organic transformations [J].

Chaudhary, Hiren R. ;

Patel, Divyang M. .

RSC ADVANCES, 2024, 14 (42) :31072-31116

[7] Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt [J].

Daw, Prosenjit ;

Ben-David, Yehoshoa ;

Milstein, David .

ACS CATALYSIS, 2017, 7 (11) :7456-7460

[8] The Green ChemisTREE: 20 years after taking root with the 12 principles [J].

Erythropel, Hanno C. ;

Zimmerman, Julie B. ;

de Winter, Tamara M. ;

Petitjean, Laurene ;

Melnikov, Fjodor ;

Lam, Chun Ho ;

Lounsbury, Amanda W. ;

Mellor, Karolina E. ;

Jankovic, Nina Z. ;

Tu, Qingshi ;

Pincus, Lauren N. ;

Falinski, Mark M. ;

Shi, Wenbo ;

Coish, Philip ;

Plata, Desiree L. ;

Anastas, Paul T. .

GREEN CHEMISTRY, 2018, 20 (09) :1929-1961

[9] Introducing Fe3O4 @SiO2 @KCC-1@MPTMS@CuII catalytic applications for the green one-pot syntheses of 2-aryl(or heteroaryl)-2,3-dihydroquinazolin-4(1 H )-ones and 9-aryl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1 H-xanthene-1,8(2H)-diones [J].

Galehban, Morteza Hasanpour ;

Zeynizadeh, Behzad ;

Mousavi, Hossein .

JOURNAL OF MOLECULAR STRUCTURE, 2023, 1271

[10] Diverse and efficient catalytic applications of new cockscomb flower-like Fe3O4aSiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite in the environmentally benign reduction and reductive acetylation of nitroarenes and one-pot synthesis of some coumarin compoundst [J].

Galehban, Morteza Hasanpour ;

Zeynizadeh, Behzad ;

Mousavi, Hossein .

RSC ADVANCES, 2022, 12 (18) :11164-11189

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