Halide Perovskite Induces Halogen/Hydrogen Atom Transfer (XAT/HAT) for Allylic C‐H Amination DOI Creative Commons

Melad Shaikh,

Kevin Rubalcaba,

Yong Yan

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 137(1)

Опубликована: Сен. 4, 2024

Abstract Allylic C−H amination has emerged as a powerful tool to construct allylamines, common motifs in molecular therapeutics. Such reaction implies an oxidative path for activation but furnishes reductive amines, inferring mild oxidants’ inactivity oxidation strong detriment products. Herein we report heterogeneous catalytic approach that manipulates halogen‐vacancies of perovskite photocatalyst and exploits halogenated‐solvents (i.e. CH 2 Cl , Br ) oxidants selective allyl with 19,376 turnovers. CsPbBr 3 nanocrystals induce cooperative hydrogen‐atom‐transfer (HAT, oxidation, halogen‐vacancy 3−x formation) halogen‐atom‐transfer (XAT, ‐induced solvent reduction) under radical chain mechanism. Terminal/internal olefins are amenable forge aromatic/aliphatic, cyclic/acyclic, secondary/tertiary allylamines (70 examples), including drugs or their derivatives.

Язык: Английский

Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation DOI
Eusebio Juaristi, C.G. Ávila-Ortíz

Synthesis, Год журнала: 2023, Номер 55(16), С. 2439 - 2459

Опубликована: Май 3, 2023

Abstract Although known for millennia, it is only recently that mechanochemistry has received serious attention by chemists. Indeed, during the past 15 years an extraordinary number of reports concerning solid-state chemical transformations through grinding and milling techniques have been recorded. This short review discusses circumstances led this renaissance, highlighting present intense interest in so-called green chemistry, enabling capacity to handle insoluble substrates, identification profound influence additives can on mechanochemically activated reactions. The core account focuses salient developments synthetic organic especially amino acid peptide­ mechanosynthesis, successful employment mechanochemical activation combination with asymmetric organocatalysis, promising enzymatic whole cell biocatalysis, remarkable achievement multicomponent selective reactions via complex, multistep reaction pathways, mechanosynthesis representative heterocycles. final section comments some pending tasks area, such as scaling-up processes be practical use industry, requirement easier more efficient control parameters monitoring devices, consequently careful analysis additional procedures a proper understanding phenomena. 1 Introduction 2 Brief History Mechanochemistry 3 Milling Equipment Reaction Parameters 4 Attributes That Propelled Its Present Renaissance 4.1 Enormous Attention Being Presently Paid Sustainable Chemistry 4.2 Reduced Energy Consumption 4.3 Additive-Based 4.4 Handling Insoluble Reactants 4.5 ‘Impossible’ Reactions Are Successful 4.6 Air- Water-Sensitive Reagents Ball 5 Salient Developments Mechanochemical Activation Synthetic Organic 5.1 Amino Acid Peptide Mechanosynthesis 5.2 Asymmetric Synthesis Organocatalysis under Ball-Milling Conditions 5.3 Mechanoenzymology 5.4 Multicomponent Activated 5.5 Heterocycles Modification 6 Future Directions 6.1 Scaling-Up Protocols 6.2 Temperature-Controlled 6.3 Understanding Transformations 6.4 Emerging Techniques 7 Conclusions

Язык: Английский

Процитировано

52
Halide Perovskite Induces Halogen/Hydrogen Atom Transfer (XAT/HAT) for Allylic C‐H Amination DOI Creative Commons

Melad Shaikh,

Kevin Rubalcaba,

Yong Yan

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 64(1)

Опубликована: Сен. 4, 2024

Allylic C-H amination has emerged as a powerful tool to construct allylamines, common motifs in molecular therapeutics. Such reaction implies an oxidative path for activation but furnishes reductive amines, inferring mild oxidants' inactivity oxidation strong detriment products. Herein we report heterogeneous catalytic approach that manipulates halogen-vacancies of perovskite photocatalyst and exploits halogenated-solvents (i.e. CH

Язык: Английский

Процитировано

4
Recent advances in biocatalytic C–N bond-forming reactions DOI

Hong-Ning Yin,

Pengcheng Wang, Zhen Liu

и другие.

Bioorganic Chemistry, Год журнала: 2024, Номер 144, С. 107108 - 107108

Опубликована: Янв. 8, 2024

Язык: Английский

Процитировано

3
Application of Imine Reductase in Bioactive Chiral Amine Synthesis DOI
Zhi Wang,

Guang-Sheng Gao,

Ya-Dong Gao

и другие.

Organic Process Research & Development, Год журнала: 2024, Номер 28(8), С. 3035 - 3054

Опубликована: Июль 11, 2024

Язык: Английский

Процитировано

3
Biocatalytic Reduction of Double Carbon-Nitrogen Bonds Toward Chiral Amines DOI

J. González-Rodríguez,

Florian Rudroff

Elsevier eBooks, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Evolution and Impact of Imine Reductases (IREDs) Research: A Knowledge Mapping Approach DOI

Qilong Yao,

Yujun Hu,

Ziwei Liu

и другие.

Molecular Biotechnology, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

Язык: Английский

Процитировано

0
Synthesis of C–N bonds by nicotinamide-dependent oxidoreductase: an overview DOI
Tianfu Wu, Wanqing Wei, Changzheng Gao

и другие.

Critical Reviews in Biotechnology, Год журнала: 2024, Номер unknown, С. 1 - 25

Опубликована: Сен. 4, 2024

Compounds containing chiral C-N bonds play a vital role in the composition of biologically active natural products and small pharmaceutical molecules. Therefore, development efficient convenient methods for synthesizing compounds is crucial area research. Nicotinamide-dependent oxidoreductases (NDOs) emerge as promising biocatalysts asymmetric synthesis due to their mild reaction conditions, exceptional stereoselectivity, high atom economy, environmentally friendly nature. This review aims present structural characteristics catalytic mechanisms various NDOs, including imine reductases/ketimine reductases, reductive aminases, EneIRED, amino acid dehydrogenases. Additionally, highlights protein engineering strategies employed modify substrate specificity, cofactor preference NDOs. Furthermore, applications NDOs essential medicinal chemicals, such noncanonical acids amine compounds, are extensively examined. Finally, outlines future perspectives by addressing challenges discussing potential utilizing establish biosynthesis platforms bond synthesis. In conclusion, provide an economical, efficient, toolbox bonds, thus contributing significantly field chemical development.

Язык: Английский

Процитировано

1
Halide Perovskite Induces Halogen/Hydrogen Atom Transfer (XAT/HAT) for Allylic C‐H Amination DOI Creative Commons

Melad Shaikh,

Kevin Rubalcaba,

Yong Yan

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 137(1)

Опубликована: Сен. 4, 2024

Abstract Allylic C−H amination has emerged as a powerful tool to construct allylamines, common motifs in molecular therapeutics. Such reaction implies an oxidative path for activation but furnishes reductive amines, inferring mild oxidants’ inactivity oxidation strong detriment products. Herein we report heterogeneous catalytic approach that manipulates halogen‐vacancies of perovskite photocatalyst and exploits halogenated‐solvents (i.e. CH 2 Cl , Br ) oxidants selective allyl with 19,376 turnovers. CsPbBr 3 nanocrystals induce cooperative hydrogen‐atom‐transfer (HAT, oxidation, halogen‐vacancy 3−x formation) halogen‐atom‐transfer (XAT, ‐induced solvent reduction) under radical chain mechanism. Terminal/internal olefins are amenable forge aromatic/aliphatic, cyclic/acyclic, secondary/tertiary allylamines (70 examples), including drugs or their derivatives.

Язык: Английский

Процитировано

0