JOURNAL OF ORGANIC CHEMISTRY
·
2025
·
IF 3.6
Haiyang Wang,Fujun Li,Wenbo Yang,Yuchao Wang,Alexander A. Miskevich,Valery A. Loiko,Lijing Zhang,Shengyang Tao
The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C–N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives to determine their effects on the synthesis of diarylamines in a flow photochemical system. Notably, n-hexylamine demonstrated the most significant promotional effect. Spectroscopic studies and experimental data reveal n-hexylamine substitutes DABCO as a Ni catalyst ligand, enhancing yields particularly in sterically hindered arylamines.
研究领域:
有机化学
·
合成化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Molecular Catalysis
·
2024
·
IF 3.9
Xin-Ni Shao,Yin-Feng Wang,Ming-Yu Qi,Zi-Rong Tang
Simultaneous utilization of photogenerated electrons and holes within a photoredox system enables effective hydrogen (H 2 ) production and organic synthesis, aligning with eco-friendly chemistry principles and current energy challenges. Here, we report the preparation and application of cocatalyst MoS 2 decorated CdS (MoS 2 CdS) composites for the photoredox-mediated C–N coupling of amines to imines and H 2 generation under visible light illumination. The H 2 and N-benzylidenebenzylamine yields for the optimal MoS 2 CdS are 28.9 and 15.0 times higher than those of bare CdS, respectively. Mechanism studies reveal that the enhanced photocatalytic activity results from the MoS 2 acting as an electron sink, which accelerates the separation and migration of photogenerated charge carriers. Additionally, the pH(•CH)NH 2 intermediates are found to play a pivotal role in the dehydrogenative coupling of benzylamine. Furthermore, the MoS 2 CdS composites exhibit universal applicability in the conversion of various aromatic amines into corresponding imines integrated with H 2 evolution.
研究领域:
化学
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材料科学
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能源科学
✓ 已验证
产品关联
DOI
高影响因子
APPLIED ORGANOMETALLIC CHEMISTRY
·
2013
·Vol. 27
·期 6
·337-340
·
IF 2.011
Junyu Dong,Tianbin Li,Chuan Dai,Wen Weng,Xinghua Xue,Yuyu Zhang,Qingle Zeng
A straightforward, protecting-group-free protocol for the synthesis of chiral 6-substituted and 6,6’-disubstituted binols (binol = 1,1’-bi-2-naphthol) by palladium-catalyzed hydroxylation, C–N and C–O coupling of chiral 6-bromo- and 6,6’ -dibromo-1,1’-binaphthols is developed. The protecting group free palladium-catalyzed hydroxylation, C–O and C–N cross-coupling protocol affords a straightforward and general method for the synthesis of chiral 6-substituted and 6,6’-disubstituted binols with good yields, avoiding the tedious procedures of introduction and removal of protecting groups. Copyright © 2013 John Wiley & Sons, Ltd.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
Industrial Chemistry & Materials
·
2023
·
IF 0
Yu Chen,Chang-Long Tan,Jing-Yu Li,Ming-Yu Qi,Zi-Rong Tang,Yi-Jun Xu
Photocatalytic hydrogen (H2) production coupled with selective oxidation of organic compounds into high-value-added organic intermediates has expansive prospects in the utilization and transformation of solar energy, which meets the development requirements of green chemistry. In this work, high-efficiency hole cocatalyst PdS-decorated In2S3 flower-like microspheres are fabricated for the effective visible-light-driven C–N coupling of amines to imines coupled with H2 evolution. Owing to the establishment of the internal electric field, which further boosts the transfer of photoexcited holes to PdS, PdS–In2S3 exhibits distinctly enhanced photocatalytic redox performance, which is 39.8 times higher for H2 and 14.3 times higher for N-benzylidenebenzylamine than that of the blank In2S3, along with high selectivity and stability. Furthermore, the practicability of dehydrogenation coupling of various aromatic amines to the corresponding C–N coupling products on PdS–In2S3 has been demonstrated and a plausible reaction mechanism has been proposed. This work is anticipated to stimulate further interest in establishing an innovative photoredox platform for selective organic synthesis coupled with H2 evolution in a green and sustainable way.
研究领域:
材料科学
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化学工程
·
环境科学
✓ 已验证
DOI
JOURNAL OF CATALYSIS
·
2024
·
IF 6.5
Huali Zhang,Xiaoxiao Chen,Jiajia Cheng,Xintuo Yang,Wei Lin,Yidong Hou,Guigang Zhang,Xinchen Wang
The integration of heterogeneous photocatalysts with nickel catalysis is garnering considerable interest for their capacity to enable distinct metal-photoredox processes for organic synthesis. However, the challenge about robustness and recyclability of the photocatalyst persists. Herein, a crystalline carbon nitride (MCN-B) photocatalyst with intentionally introduced defects and a dedicated designed active site has been presented. Results reveal by incorporating the deprotonated cyano-group (N - –CN) sites, this host material could provide stable binding sites for Ni (II) ions through the Hard-Soft Acid-Base (HSAB) effect, thereby facilitating charge transmission between semiconductor and metal centers. Consequently, the integrated carbon nitride nickel (Ni/MCN-B) heterogeneous photocatalyst demonstrates high effectiveness in diverse photocatalytic C-N coupling reactions (21 examples, up to 93% yield) under conditions free from organic ligands and additives, which shows competent performance to the homogeneous catalysts. Moreover, the Ni/MCN-B catalyst demonstrates remarkable recyclability, maintaining its photoredox efficiency after 10 cycles with minimal loss of activity and a diminished metal leaching rate, which signifies a substantial advancement in the field of photocatalytic system design.
研究领域:
有机化学
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材料科学
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催化反应
✓ 已验证
产品关联
DOI
高影响因子
APPLIED ORGANOMETALLIC CHEMISTRY
·
2018
·Vol. 32
·期 10
·e4483
·
IF 3.581
Xufeng Wu,Lingyu Li,Wenlong Jiang,Lihong Zhou,Qingle Zeng
Tosylhydrazones are a kind of labile and highly reactive compounds, which are apt to be transformed into reactive diazo compounds and then into extremely reactive carbenes under the basic condition. In order to fulfil the valuable C-N coupling reaction, diaryliodonium salts are evaluated and prove to be a class of efficient electrophiles. The reaction with ligand-free copper salt as catalyst shows a wide range of substrate scope. A plausible mechanism is proposed.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2018
·Vol. 42
·期 19
·16013-16020
·
IF 3.201
Xuemin Liu,Shuo Chang,Xinzhi Chen,Xin Ge,Chao Qian
Three different types of functionalized-CS were prepared and anchored with copper salts for use as the catalyst for the Ullmann C–X coupling reaction. The Schiff-basic chitosan supported copper complex (PCCS@CuI) exhibits the highest catalytic activity. The structure of the catalyst was characterized by FTIR spectroscopy, TG, XRD, SEM, EDS and XPS. This catalyst exhibited high applicability for the C–N and C–S coupling reactions, in which good to excellent yields were obtained. Its easy separation, good reusability and stability were notable.
研究领域:
有机化学
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材料科学
✓ 已验证
产品关联
DOI
高影响因子
ORGANIC PROCESS RESEARCH & DEVELOPMENT
·
2019
·
IF 3.327
Cuiling Wang,Xiao Bai,Rui Wang,Xudong Zheng,Xiumei Ma,Huan Chen,Yun Ai,Yajun Bai,Yifeng Liu
A new method for imatinib synthesis is described by using the C–N coupling reaction of 4-(4-methylpiperazine-1-methyl)benzamide with N-(5-bromo-2-tolyl)-4-(3-pyridyl)pyrimidin-2-amine to form imatinib. In this synthetic route, the high efficiency and high selectivity of nano-ZnO as a catalyst is key to the mild hydrolysis of 4-(4-methylpiperazine-1-methyl)benzonitrile into the corresponding amide. The total imatinib yield was 51.3%, and the purity was 99.9%. This simple and effective synthetic pathway avoids gene-impurity production (as classified by the FDA Center for Drug Evaluation and Research), and the synthesis is environmentally friendly with a short reaction time.
研究领域:
药物化学
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有机合成
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催化化学
✓ 已验证
产品关联
DOI
高影响因子
TETRAHEDRON
·
2014
·
IF 2.817
Dazhuang Miao,Xuesong Shi,Guozhen He,Yao Tong,Zengqiang Jiang,Shiqing Han
N -(2-Chloro-phenyl)-2-halo-benzamides (halo=I/Br/Cl) as substrates were used for the one-pot synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed intermolecular C–N/intramolecular C–O couplings with primary amines . This aryl amination offers clean reaction conditions and easy work-up in good yields by using CuI as catalyst, readily available 8-hydroxyquinoline as ligand, K 3 PO 4 as base, DMF as solvent.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
SYNTHESIS-STUTTGART
·
2015
·Vol. 47
·期 23
·3751-3757
·
IF 2.689
Zhijie Li,Quan Wen,Lihong Zhou,Xingmei Deng,Qingle Zeng
The synthesis of highly important α-hydroxycarboxylic acid anilides via copper-catalyzed chemoselective C–N coupling reactions of α-hydroxyamides and aryl halides is described. This highly selective N-arylation process demonstrates wide substrate scope, cost savings and easy operation. In addition, the chirality of l-3-phenyllactamide is preserved during the reaction.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2015
·Vol. 40
·期 2
·1454-1459
·
IF 3.086
Limei Zhou,Mengyun Yin,Xiaohui Jiang,Qiang Huang,Wencheng Lang
1,3-Diamino-graphene (NH2-G-NH2) materials were synthesized using a simple chemical method. The as-prepared materials were characterized using FT-IR, TG, XRD, XPS, and SEM measurements. The results revealed that a 1,3-diamino group was successfully grafted on graphene and could immobilize CuI by coordination interactions. The NH2-G-NH2 materials can be used as heterogeneous ligands for CuI-catalyzed C–N coupling reactions, and the desired products were obtained with good yields. The reaction system is much smoother at lower temperature compared with others previously reported. Additionally, the new method can easily realize the purification of products and recycling of catalysts.
研究领域:
材料科学
·
有机化学
·
催化化学
✓ 已验证
DOI
高影响因子
ACS Nano
·
2022
·
IF 18.027
Yujun Zhang,Shenghua Ye,Min Gao,Yong Li,Xuan Huang,Jun Song,Hong Cai,Qianling Zhang,Junmin Zhang
Heterogenization of homogeneous catalysis through supported single-atom catalysts (SACs) provided a feasible solution to recycling catalysts while keeping its efficiency in chemical synthesis. In this work, Cu SACs anchored on N-doped graphene (Cu SACs/NG) were prepared and first used for C–N coupling reactions. During the preparation, Cu–N–C structures, including Cu–N4 moieties, were formed in a one-step pyrolysis method. As-prepared Cu SACs/NG exhibited excellent catalytic activity toward C–N coupling reactions with a broad scope of substrates and showed outstanding performance of recycling. Compared with Cu nanoparticles (Cu NPs/NG), the advantages of single-atom catalysts were validated via experimental and theoretical calculations. The enhanced performances were attributed to increasing the number of active sites and increasing the intrinsic activity of each active site. This work provides an alternative synthetic strategy for fabricating atomically dispersed SACs and represents a significant advance for coupling reactions.
研究领域:
材料科学
·
催化化学
✓ 已验证
DOI
高影响因子
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