Fe3O4@TiO2 nanoparticles catalyzed and NaBH4 assisted one-pot reductive amination of aldehydes at ambient condition

被引:2
作者
Pinjari, Sajid [1 ,2 ]
Shirole, Gopinath [3 ]
Uphade, Bhagwat [1 ,2 ]
Gadhave, Anil [1 ,2 ]
机构
[1] Savitribai Phule Pune Univ, Padmashri Vikhe Patil Coll, Dept Chem, Pravaranagar 413713, MS, India
[2] Savitribai Phule Pune Univ, Padmashri Vikhe Patil Coll, Res Ctr, Pravaranagar 413713, Maharashtra, India
[3] Arts Sci & Commerce Coll, Dept Chem, Rahata, MS, India
关键词
Fe3O4; TiO2; nanoparticles; NaBH4; Reductive amination; One-pot reaction; CARBONYL-COMPOUNDS; HIGHLY EFFICIENT; SECONDARY-AMINES; FORMIC-ACID; MILD; KETONES; COMPOSITE; DABCO; BIS;
D O I
10.1007/s11164-023-05123-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An operationally convenient and efficient one-pot reductive amination of diversely substituted aldehydes catalyzed by Fe3O4@TiO2 nanoparticles and NaBH4 as a reductant in ethanol at ambient condition is reported in this work. The structural features of Fe3O4@TiO2 nanoparticles are explored by various tools like FT-IR, XRD, TEM, FE-SEM and EDX techniques. The heterogeneous nature, good catalytic potential and reusability are some of the important attributes of the catalyst. The beneficial features of this procedure are one-pot reaction, short reaction time, low catalyst requirement, applicability to wide range of substrates with good yields, milder and simple reaction condition. The structures of synthesized amine derivatives were established by H-1-NMR, C-13-NMR and HR-MS spectral analysis.
引用
收藏
页码:4973 / 4996
页数:24
相关论文
共 69 条
[1]   Hybrid organic-inorganic Cu(II) iminoisonicotine@TiO2@Fe3O4 heterostructure as efficient catalyst for cross-couplings [J].
Adam, Mohamed Shaker S., I ;
Ullah, Farman ;
Makhlouf, Mohamed M. .
JOURNAL OF THE AMERICAN CERAMIC SOCIETY, 2020, 103 (08) :4632-4653
[2]   Reductive Amination in the Synthesis of Pharmaceuticals [J].
Afanasyev, Oleg, I ;
Kuchuk, Ekaterina ;
Usanov, Dmitry L. ;
Chusov, Denis .
CHEMICAL REVIEWS, 2019, 119 (23) :11857-11911
[3]   Selective Buchwald-Hartwig arylation of C-amino-1,2,4-triazoles and other coordinating aminoheterocycles enabled by bulky NHC ligands and TPEDO activator [J].
Astakhov, Alexander V. ;
Chernenko, Andrey Yu. ;
Kutyrev, Vadim V. ;
Ranny, Gleb S. ;
Minyaev, Mikhail E. ;
Chernyshev, Victor M. ;
Ananikov, Valentine P. .
INORGANIC CHEMISTRY FRONTIERS, 2022, 10 (01) :218-239
[4]   An expedient and straightforward solvent-free synthesis of 1,8-dioxo-octahydroxanthenes using eco-friendly aluminized polyborate catalyst [J].
Aute, Dilip ;
Kshirsagar, Akshay ;
Uphade, Bhagwat ;
Gadhave, Anil .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (10) :3691-3702
[5]   Aluminized polyborate-catalysed green and efficient synthesis of polyhydroquinolines under solvent-free conditions [J].
Aute, Dilip ;
Kshirsagar, Akshay ;
Uphade, Bhagwat ;
Gadhave, Anil .
RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (07) :3491-3508
[6]   Benzylmorpholine Analogs as Selective Inhibitors of Lung Cytochrome P450 2A13 for the Chemoprevention of Lung Cancer in Tobacco Users [J].
Blake, Linda C. ;
Roy, Anuradha ;
Neul, David ;
Schoenen, Frank J. ;
Aube, Jeffrey ;
Scott, Emily E. .
PHARMACEUTICAL RESEARCH, 2013, 30 (09) :2290-2302
[7]   Development of an Effective Scalable Enantioselective Synthesis of the HIV-1 Entry Inhibitor BNM-III-170 as the Bis-trifluoroacetate Salt [J].
Chen, Junhua ;
Park, Jun ;
Kirk, Sharon M. ;
Chen, Hung-Ching ;
Li, Xiangqin ;
Lippincott, Daniel J. ;
Melillo, Bruno ;
Smith, Amos B., III .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (11) :2464-2469
[8]   Protecting-Group-Free Synthesis of Amines: Synthesis of Primary Amines from Aldehydes via Reductive Amination [J].
Dangerfield, Emma M. ;
Plunkett, Catherine H. ;
Win-Mason, Anna L. ;
Stocker, Bridget L. ;
Timmer, Mattie S. M. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) :5470-5477
[9]   Zinc-Catalyzed Chemoselective Reduction of Tertiary and Secondary Amides to Amines [J].
Das, Shoubhik ;
Addis, Daniele ;
Junge, Kathrin ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (43) :12186-12192
[10]   Sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe2O3 nanocrystallites as a magnetically separable catalyst for one-pot reductive amination of carbonyl compounds [J].
Deng, Jia ;
Mo, Li-Ping ;
Zhao, Fei-Yang ;
Hou, Lan-Lan ;
Yang, Li ;
Zhang, Zhan-Hui .
GREEN CHEMISTRY, 2011, 13 (09) :2576-2584