Deprotonation-Induced Phase Transitions in the Self-Assembled Structure of Prochiral Carboxyl Derivatives

Chen, Ran; Song, Huawei; Zhu, Han; Zhou, Xuhan; Li, Peigen; Ji, Yi; Ji, Hongbing; Chen, Shenwei

doi:10.1021/acs.jpcc.2c02313

Cited by 5 publications

(4 citation statements)

References 50 publications

(63 reference statements)

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“…In 2019, the Zhu group reported a metal-free approach to the synthesis of γ-lactams that involves intramolecular nitration-aminocarbonylation of unactivated alkenes 133 (Scheme 33 ). 71 Under the reaction conditions, unexpected γ-lactams were formed instead of cyano-migrated products. According to the experimental results and mechanistic investigations, the transformation involves the addition of a nitro radical to alkene 133 followed by an intramolecular capture of alkyl radical 135 by the cyano group to afford five-membered cyclic intermediate 136 .…”

Section: Organic Nitrating Reagentsmentioning

confidence: 98%

Organic Nitrating Reagents

Patra¹,

Mosiagin²,

Katayev³

et al. 2022

Synthesis

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Nitro compounds are vital raw chemicals that are widely used in academic laboratories and industries for the preparation of various drugs, agrochemicals, and materials. Thus, nitrating reactions are of great importance for chemists and are even taught in schools as one of the fundamental transformations in organic synthesis. Since the discovery of the first nitrating reactions in the 19th century, progress in this field has been constant. Yet, for many years the classical electrophilic nitration approach using a mixture of strong mineral acids dominated the field. However, in recent decades, the attention of researchers has focused on new reactivity and new reagents that can provide access to nitro compounds in a practical and straightforward way under mild reaction conditions. Organic nitrating reagents have played a special role in this field since they have enhanced reactivity. They also allow nitration to be carried out in an ecofriendly and sustainable manner. This review examines the development and application of organic nitrating reagents.1 Introduction2 Organic Nitrating Reagents2.1 Alkyl Nitrites2.2 Nitroalkanes2.3 Alkyl Nitrates2.4 N-Nitroamides2.5 N-Nitropyrazole2.6 N-Nitropyridinium Salts3 Organic Nitrating Reagents Generated In Situ3.1 Acyl Nitrates3.2 Trimethylsilyl Nitrate3.3 Nitro Onium Salts4 Organic Nitronium Salts5 Organic Nitrates and Nitrites5.1 Ammonium Nitrates5.2 Heteroarylium Nitrates5.3 Other Organic Nitrates5.4 Organic Nitrites6 Conclusion and Outlook

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Section: Organic Nitrating Reagentsmentioning

confidence: 98%

Organic Nitrating Reagents

Patra¹,

Mosiagin²,

Katayev³

et al. 2022

Synthesis

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“…A great number of chiral assemblies have been studied on metal surfaces, including 0D chiral clusters, [24][25][26][27] 1D chiral chains, stripes or lines, filaments, wires [28][29][30][31][32][33][34] and 2D chiral islands, lamellas structures and honeycomb or more complex nontrivial architectures (chiral Kagome networks, quasicrystals, Sierpiński triangle fractals and semi-regular Archimedean tilings) that may possess intriguing physical and chemical properties. Most of these chiral nanostructures are achieved through shortrange chiral recognition induced by non-covalent intermolecular interactions, such as hydrogen bonding, [24,28,30,31,[34][35][36][37][38][39][40][41][42] halogen bonding, [33,[43][44][45][46] van der Waals (vdW) forces, [47] dipoledipole interactions, [48] metal-organic coordination [33,[49][50][51] or cooperative interactions of two or more sorts of intermolecular forces. [27,29,34,40,[52][53][54][55] In addition, the competition between molecule-molecule an...…”

Section: Chiral Assemblies Induced By Short-range Chiral Recognitionmentioning

confidence: 99%

From Short‐ to Long‐Range Chiral Recognition on Surfaces: Chiral Assembly and Synthesis

Peng,

Zhang,

Liu

et al. 2023

Small

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Research on chiral behaviors of small organic molecules at solid surfaces, including chiral assembly and synthesis, can not only help unravel the origin of the chiral phenomenon in biological/chemical systems but also provide promising strategies to build up unprecedented chiral surfaces or nanoarchitectures with advanced applications in novel nanomaterials/nanodevices. Understanding how molecular chirality is recognized is considered to be a mandatory basis for such studies. In this review, a series of recent studies in chiral assembly and synthesis at well‐defined metal surfaces under ultra‐high vacuum conditions are outlined. More importantly, the intrinsic mechanisms of chiral recognition are highlighted, including short/long‐range chiral recognition in chiral assembly and two main strategies to steer the reaction pathways and modulate selective synthesis of specific chiral products on surfaces.

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“…At the same time, our group 41 reported a cobalt-catalyzed AH of 1,1-diarylethenes using the chiral oxazoline iminopyridine (OIP) ligated cobalt complex Co-11 as a precatalyst (Scheme 5a ). A series of substituted 1,1-diarylethenes (32 examples) were successfully converted into chiral products in high yields (77–99%) and with high enantioselectivities (>90% ee in most cases) under 1 atm of H 2 at room temperature in the presence of 15 mol% of NaBHEt 3 as an activator.…”

Section: Co-catalyzed Ah Of Minimally Functionalized Alkenesmentioning

confidence: 99%

Earth-Abundant Transition Metal Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Alkenes

2022

Synthesis

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Transition-metal-catalyzed asymmetric hydrogenation (AH) continues to be a growing field and a fundamental tool to construct chiral compounds. The use of earth‐abundant transition metals in AH reactions remains generally limited, but has received increasing attention in recent years due to cost, sustainability, and environmental concerns. Here, we will summarize the progress in first-row transition metal-catalyzed AH of minimally functionalized alkenes, including scopes, mechanisms, and the challenges in this field.

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Deprotonation-Induced Phase Transitions in the Self-Assembled Structure of Prochiral Carboxyl Derivatives

Cited by 5 publications

References 50 publications

Organic Nitrating Reagents

Organic Nitrating Reagents

From Short‐ to Long‐Range Chiral Recognition on Surfaces: Chiral Assembly and Synthesis

Earth-Abundant Transition Metal Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Alkenes

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