Base Promoted Hydrogenation of N-Heteroarenes with Ammonia Borane and DMSO DOI
Dongxu Jia, Zhenkang Ai,

Xinya Yuan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

Herein, we report a sodium tert-butoxide-promoted reduction of N-heteroarenes using ammonia borane and dimethyl sulfoxide (DMSO) under mild reaction conditions. This method demonstrates broad functional group compatibility across diverse N-heteroarene substrates. Notably, substituting DMSO with deuterated DMSO-d6 enables the synthesis C3-deuterated 1,2,3,4-tetrahydroquinolines remarkable positional selectivity. Mechanistic investigations indicate that protons are derived from both DMSO. strategy establishes novel environmentally benign approach for (deuterated) N-heterocycles, offering practical advantages in terms operational simplicity sustainable

Language: Английский

Lanthanide/B(C6F5)3-Promoted Hydroboration Reduction of Indoles and Quinolines with Pinacolborane DOI
Jianping Zhang, Ziyan Chen, Mingxin Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 887 - 897

Published: Jan. 5, 2024

We have developed a lanthanide/B(C6F5)3-promoted hydroboration reduction of indoles and quinolines with pinacolborane (HBpin). This reaction provides streamlined access to range nitrogen-containing compounds in moderate excellent yields. Large-scale synthesis further transformations bioactive indicate that the method has potential practical applications. Preliminary mechanistic studies suggest amine additives promote formation indole-borane intermediates, proceeds via intermediates HBpin situ-formed BH3 species, followed by protodeborylation process.

Language: Английский

Citations

7
Precise Distance Control and Functionality Adjustment of Frustrated Lewis Pairs in Metal–Organic Frameworks DOI
Wenhao Chen, Shenhui Li, Lezhi Yi

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(17), P. 12215 - 12224

Published: April 17, 2024

We report the construction of frustrated Lewis pairs (FLPs) in a metal-organic framework (MOF), where both acid (LA) and base (LB) are fixed to backbone. The anchoring tritopic organoboron linker as LA monotopic LB separate metal oxide clusters tetrahedron geometry allows for precise control distance between them. As type varies, pyridine, phenol, aniline, benzyl alcohol, series 11 FLPs were constructed give distances 7.1, 5.5, 5.4, 4.8 Å, respectively, revealed by

Language: Английский

Citations

7
Radiation‐Synthesized Metal–Organic Frameworks with Ligand‐Induced Lewis Pairs for Selective CO2 Electroreduction DOI
Wenhui Liu, Bijun Tang, Kai Huang

et al.

Small, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 15, 2024

Abstract The electrochemical activation of inert CO 2 molecules through C─C coupling reactions under ambient conditions remains a significant challenge but holds great promise for sustainable development and the reduction emission. Lewis pairs can capture react with , offering novel strategy electrosynthesis high‐value‐added C2 products. Herein, an electron‐beam irradiation is presented rapidly synthesizing metal–organic framework (MOF) well‐defined (i.e., Cu‐ N pyridinic ). synthesized MOFs exhibit total product faradic efficiency 70.0% at −0.88 V versus RHE. In situ attenuated reflection Fourier transform infrared Raman spectra reveal that electron‐deficient acidic Cu sites electron‐rich basic in ligand facilitate targeted chemisorption, activation, conversion molecules. DFT calculations further elucidate electronic interactions key intermediates reaction. work not only advances pair‐site as new platform conversion, also provides pioneering insights into underlying mechanisms irradiated synthesis advanced nanomaterials.

Language: Английский

Citations

7
Ultrahigh Stable Heterometallic InCo-Organic Framework for Efficiently Catalyzing Cycloaddition of CO2 with Epoxides and Knoevenagel condensation DOI
Xiaotong Wang, Chong Li,

Tuoping Hu

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1318, P. 139223 - 139223

Published: July 6, 2024

Language: Английский

Citations

6
Engineering Interfacial Low-Coordinated Mg3C2+-O3C2– Lewis Acid–Base Pairs on MgO for Cycloaddition of CO2 with Epoxides DOI

Juncong Yuan,

Ranfei Fu,

Zeping Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(14), P. 11045 - 11050

Published: July 9, 2024

Language: Английский

Citations

6
Engineering Frustrated Lewis Pair Active Sites in Porous Organic Scaffolds for Catalytic CO2 Hydrogenation DOI Creative Commons
Shubhajit Das, Rubén Laplaza, J. Terence Blaskovits

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(23), P. 15806 - 15814

Published: May 30, 2024

Frustrated Lewis pairs (FLPs), featuring reactive combinations of acids and bases, have been utilized for myriad metal-free homogeneous catalytic processes. Immobilizing the active sites to a solid support, especially porous scaffolds, has shown great potential ameliorate FLP catalysis by circumventing some its inherent drawbacks, such as poor product separation catalyst recyclability. Nevertheless, designing immobilized pair (LPASs) is challenging due requirement placing donor acceptor centers in appropriate geometric arrangements while maintaining necessary chemical environment perform catalysis, clear design rules not yet established. In this work, we formulate simple guidelines build highly LPASs direct hydrogenation CO2 through large-scale screening diverse library 25,000 FLPs. The built introducing boron-containing acidic vicinity existing basic nitrogen organic linkers metal–organic frameworks collected "top-down" fashion from CoRE MOF 2019 database. geometrical appropriateness these determined evaluating series descriptors representing intrinsic strength (acidity basicity) components their spatial arrangement sites. Analysis leading candidates enables formulation pragmatic experimentally relevant principles which constitute starting point further exploration FLP-based catalysts reduction CO2.

Language: Английский

Citations

5
Amino-functionalized MOF-based fluorescent sensor for efficient detection of 3-nitrotyrosine in serum DOI

Lixiang Chen,

Lingshan Gong, Ya Ping Wang

et al.

Inorganic Chemistry Communications, Journal Year: 2024, Volume and Issue: 167, P. 112787 - 112787

Published: June 27, 2024

Language: Английский

Citations

5
Selective detection of food contaminants using engineered gallium-organic frameworks with MD and metadynamics simulations DOI Creative Commons

Somayeh Hamsayegan,

‪Heidar Raissi, Afsaneh Ghahari

et al.

Scientific Reports, Journal Year: 2024, Volume and Issue: 14(1)

Published: Aug. 5, 2024

The exclusion mechanism of food contaminants such as bisphenol A (BPA), Flavonoids (FLA), and Goitrin (GOI) onto the novel gallium-metal organic framework (MOF) functionalized MOF with oxalamide group (MOF-OX) is evaluated by utilizing molecular dynamics (MD) Metadynamics simulations. atoms in molecules (AIM) analysis detected different types atomic interactions between contaminant substrates. To assess this procedure, a range descriptors including interaction energies, root mean square displacement, radial distribution function (RDF), density, hydrogen bond count (HB), contact numbers are examined across simulation trajectories. most important elements stability systems under examination found to be stacking π-π HB interactions. It was confirmed significant value total energy for BPA/MOF-OX (- 338.21 kJ mol

Language: Английский

Citations

5
Covalent Organic Framework-Derived B/N Co-Doped Carbon FLPs Metal-Free Catalysts for the Selective Hydrogenation of α,β-Unsaturated Aldehydes to Unsaturated Alcohols DOI
Linhao Zhong,

Xiaoqing Liao,

Haishuai Cui

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15799 - 15810

Published: Oct. 10, 2024

An ongoing challenge is to precisely tailor the frustrated Lewis pairs (FLPs) sites construct all-solid-state FLPs metal-free catalysts that are as effective or even more than homogeneous/metal in H2 activation. In this study, B/N codoped carbon (SNW-BCN) were prepared by tailoring targeted doping of B atoms nitrogen-rich covalent organic framework (SNW-1) using ligand-exchange strategy and self-templated carbonization. The then applied selective hydrogenation α,β-unsaturated aldehydes unsaturated alcohols. It was found a significant amount pyridinic-N could be obtained from SNW-1. Moreover, can accomplished introducing ligands (4-formylphenylboronic acid) with acid heteroatoms pre-empt ligand site Additionally, B–N bond, which preferentially forms between neighboring N at high temperature, function site. DFT calculations situ characterizations show electron-rich electron-deficient form B–N/pyridinic-N sites, effectively activate C═O aldehydes, only 0.36 eV H–H bond dissociation energy. This work encourages environmentally friendly synthesis alcohols offers fresh concepts for development catalysts. experiments on catalyst scale-up also investigated because they might shed light production large scale.

Language: Английский

Citations

4
Unique H2O Vortex in One New MOF Material Strengthening C3H6 Adsorption and Unprecedented Purification from C2H4/C3H8/C3H6 Mixtures DOI Open Access
Lin Zhang,

Ruicheng Gao,

Xin Liu

et al.

Advanced Functional Materials, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 5, 2025

Abstract The gradual separation of the naphtha steam cracking product (propane/propylene/ethylene, C 3 H 8 /C 6 2 4 ) to obtain highly pure is great significance as it provides an alternative process for this important industrial feedstock. However, developing adsorbents meet efficient and purification application remains challenging. A water coordination‐decorated metal–organic framework (MOF, Cd‐dtzip‐H O) material reported. Interestingly, molecules cooperate with build a vortex significantly affect preferential adsorption . At 298 K 100 kPa, loading in 112.0 cm g −1 , equivalent 1.7 2.0 times respectively. Experimental breakthroughs show that efficiently separates under different pressures. Meanwhile, also unprecedentedly achieves one‐step mixtures yielding high‐purity (99.9%) (99.95%) products productivities 38.2 12.7 L kg

Language: Английский

Citations

0