Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water DOI
Hidemasa Hikawa,

Taku Nakayama,

Shunki Nakamura

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(20), P. 4183 - 4188

Published: Jan. 1, 2022

We report a method for gold( iii )/TPPMS-catalyzed direct amination of benzhydols using 2-aminopyridines with poor nucleophilic character in water.

Language: Английский

Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters DOI
Evgeniya Podyacheva, Oleg I. Afanasyev, Dmitry Vasilyev

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(12), P. 7142 - 7198

Published: June 1, 2022

Borrowing hydrogen or the autotransfer amination is a powerful approach to create single C–N bonds, starting from stable and readily available substrates: amines alcohols. It considered as one of most atom-efficient green methods synthesize complex amines. Herein, we attempted arrange array existing data in comprehensive structured manner determine correlations between experimental conditions catalysis outcome both within different groups catalysts defined using machine analysis. For each type N-nucleophiles (aromatic, aliphatic, heteroaromatic amines, amides), efficient working were suggested, including attributing optimal base temperature regime for metal.

Language: Английский

Citations

83
Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction DOI
Jiahao Li,

Anruo Mao,

Wei Yao

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(6), P. 2602 - 2612

Published: Jan. 1, 2022

Porous polypyridine-oxadiazole supported iridium catalysts (PPO-Ir) revealed high catalytic activity for the reaction of dimethyl-6-aminouracil (including 1,3-dimethylbarbituric acid, 2-aminobenzylamine) with alcohols.

Language: Английский

Citations

53
Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach DOI
Avijit Mondal, Rahul Sharma,

Debjyoti Pal

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(26), P. 3690 - 3720

Published: June 15, 2021

Abstract Development in the area of acceptorless dehydrogenation (AD) and borrowing hydrogen (BH) catalysis emerge as one potential tools for various C−C C‐heteroatom bond forming reactions. Alcohols, which are important lignocellulosic biomass products, act pivotal electrophilic coupling partners such processes interestingly only H 2 or O is eliminated a byproduct. Initially, was developed by use noble metal catalysts. Recently, base metals Mn, Fe, Co, Ni proved to be environmentally benign inexpensive alternatives application AD BH methods. This transition catalyzed approaches also allow access toward plethora structurally heterocyclic molecules via atom economical strategy. Herein, we summarize current rising expansion heterocycles synthesis through hydrogenation

Language: Английский

Citations

56
Dehydrogenative Synthesis of Quinolines and Quinazolines via Ligand-Free Cobalt-Catalyzed Cyclization of 2-Aminoaryl Alcohols with Ketones or Nitriles DOI
Zhiqiang Hao, Xiaoyu Zhou, Zongwen Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12596 - 12607

Published: Sept. 26, 2022

We present a convenient and efficient protocol to synthesize quinolines quinazolines in one pot under mild conditions. A variety of substituted were synthesized good excellent yields (up 97% yield) from the dehydrogenative cyclizations 2-aminoaryl alcohols ketones catalyzed by readily available Co(OAc)2·4H2O. This cobalt catalytic system also showed high activity reactions 2-aminobenzyl with nitriles, affording various quinazoline derivatives 95% yield). The offers an environmentally benign approach for synthesis N-heterocycles employing earth-abundant salt ligand-free

Language: Английский

Citations

38
Well‐Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α‐Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines DOI
Rahul Sharma, Avijit Mondal,

Arup Samanta

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(14), P. 2429 - 2437

Published: May 23, 2022

Abstract The “borrowing hydrogen” (BH) method for C‐alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst borrowing hydrogen transformation a key challenge to be witnessed. Herein we have presented synthesis of non‐phosphine, easily accessible SNS−Ni complexes. Ni‐catalyst was successfully applied the ketone enolates α‐alkylated ketones. Primary with different functional groups various heteroaromatic alcohols are well tolerated. present system efficiently gram scale also green chemistry metrics reaction were calculated. protocol extended biologically quinoline moieties. Finally, control experiments deuterium labelled suggest that proceeds via pathway. magnified image

Language: Английский

Citations

24
Electronically tuneable orthometalated RuII–NHC complexes as efficient catalysts for C–C and C–N bond formations via borrowing hydrogen strategy DOI
Praseetha Mathoor Illam, Arnab Rit

Catalysis Science & Technology, Journal Year: 2021, Volume and Issue: 12(1), P. 67 - 74

Published: Nov. 10, 2021

A series of simple and electronically tuneable cyclometalated Ru II –NHC complexes have been explored as efficient catalysts for various C–C/N bond forming reactions via a BH methodology.

Language: Английский

Citations

30
Recent advances in C/N-alkylation with alcohols through hydride transfer strategies DOI
Mahdi Jafarzadeh,

Seyed Hasan Sobhani,

Karol Gajewski

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(39), P. 7713 - 7745

Published: Jan. 1, 2022

Recent advances in C/N alkylation using alcohols as alkylating reagents via hydrogen-shuttle methodologies: Borrowing Hydrogen, Acceptorless Dehydrogenative Coupling, and Base-mediated Hydride Transfer.

Language: Английский

Citations

20
Copper-Mediated C4-Benzylations of 5-Aminopyrazoles with 3-Indoleacetic Acids DOI
Qiwen Gao, Jinhong Tian,

Kangmei Wen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6623 - 6632

Published: May 11, 2023

Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated are prepared in good-to-excellent yields under basic and ligand-free conditions the presence copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, C4-benzylated cyclized into 1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles aldehydes via one-pot two-step processes; notably, fluorescence emissions large Stokes shifts.

Language: Английский

Citations

12
Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N-alkylated aminoquinoline derivatives via the borrowing hydrogen approach DOI
Jiahao Li,

Anruo Mao,

Xinyu Hu

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(11), P. 5064 - 5072

Published: Jan. 1, 2024

Herein, we report an efficient and straightforward approach for the synthesis of

Language: Английский

Citations

4
3d Transition Metal Complexes as Homogeneous Catalysts in N-Alkylation Reactions Using Alcohols: A Recent Update DOI

Jharna Mahato,

Rima Das,

Tanmoy Saha

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 165, P. 134192 - 134192

Published: Aug. 13, 2024

Language: Английский

Citations

4