Chemical ReviewsPub Date : 2024-09-13DOI: 10.1021/acs.chemrev.4c0030310.1021/acs.chemrev.4c00303
Akira Yoshimura*, and , Viktor V. Zhdankin*,
{"title":"Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents","authors":"Akira Yoshimura*, and , Viktor V. Zhdankin*, ","doi":"10.1021/acs.chemrev.4c0030310.1021/acs.chemrev.4c00303","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00303https://doi.org/10.1021/acs.chemrev.4c00303","url":null,"abstract":"<p >Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7–8 years, between 2016 and 2024.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"124 19","pages":"11108–11186 11108–11186"},"PeriodicalIF":51.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.chemrev.4c00303","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142403141","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-13DOI: 10.1021/acs.chemrev.4c00303
Akira Yoshimura, Viktor V. Zhdankin
{"title":"Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents","authors":"Akira Yoshimura, Viktor V. Zhdankin","doi":"10.1021/acs.chemrev.4c00303","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00303","url":null,"abstract":"Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7–8 years, between 2016 and 2024.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"37 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142198100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-08DOI: 10.1021/acs.chemrev.4c00188
Xinghua Wang, Jing He, Ya-Nan Wang, Zhenyan Zhao, Kui Jiang, Wei Yang, Tao Zhang, Shiqi Jia, Kangbao Zhong, Linbin Niu, Yu Lan
{"title":"Strategies and Mechanisms of First-Row Transition Metal-Regulated Radical C-H Functionalization.","authors":"Xinghua Wang, Jing He, Ya-Nan Wang, Zhenyan Zhao, Kui Jiang, Wei Yang, Tao Zhang, Shiqi Jia, Kangbao Zhong, Linbin Niu, Yu Lan","doi":"10.1021/acs.chemrev.4c00188","DOIUrl":"10.1021/acs.chemrev.4c00188","url":null,"abstract":"<p><p>Radical C-H functionalization represents a useful means of streamlining synthetic routes by avoiding substrate preactivation and allowing access to target molecules in fewer steps. The first-row transition metals (Ti, V, Cr, Mn, Fe, Co, Ni, and Cu) are Earth-abundant and can be employed to regulate radical C-H functionalization. The use of such metals is desirable because of the diverse interaction modes between first-row transition metal complexes and radical species including radical addition to the metal center, radical addition to the ligand of metal complexes, radical substitution of the metal complexes, single-electron transfer between radicals and metal complexes, hydrogen atom transfer between radicals and metal complexes, and noncovalent interaction between the radicals and metal complexes. Such interactions could improve the reactivity, diversity, and selectivity of radical transformations to allow for more challenging radical C-H functionalization reactions. This review examines the achievements in this promising area over the past decade, with a focus on the state-of-the-art while also discussing existing limitations and the enormous potential of high-value radical C-H functionalization regulated by these metals. The aim is to provide the reader with a detailed account of the strategies and mechanisms associated with such functionalization.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"10192-10280"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141900076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-01DOI: 10.1021/acs.chemrev.3c00915
Tze-Fei Wong
{"title":"Triphasic Development of the Genetic Code.","authors":"Tze-Fei Wong","doi":"10.1021/acs.chemrev.3c00915","DOIUrl":"10.1021/acs.chemrev.3c00915","url":null,"abstract":"<p><p>The genetic code contains an alphabet of genetically encoded amino acids. The ten Phase 1 amino acids, including Gly, Ala, Ser, Asp, Glu, Val, Leu, Ile, Pro and Thr, were available from the prebiotic environment, whereas the ten Phase 2 amino acids, including Phe, Tyr, Arg, His, Trp, Asn, Gln, Lys, Cys, and Met, became available only later from amino acid biosyntheses. In the archaeon <i>Methanopyrus kandleri</i>, the oldest organism known, the standard alphabet of 20 amino acids was \"frozen\" and no additional amino acid was encoded in the subsequent 3 Gyrs. Four decades ago, it was discovered that the code was frozen because all the organisms were so well adapted to the standard amino acids that oligogenic barriers, consisting of genes that are thoroughly dependent on the standard code, would cause loss of viability upon the deletion of any one amino acid from the code. Once the reason for the freezing of the code was ascertained, procedures were devised by scientists worldwide to enable the encoding of novel noncanonical amino acids (ncAAs). These encoded Phase 3 ncAAs now surpass the 20 canonical Phase 2 amino acids in the code.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"9866-9872"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11393795/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141858205","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-27DOI: 10.1021/acs.chemrev.4c00174
Ruixia Wu, Hongmei Zhang, Huifang Ma, Bei Zhao, Wei Li, Yang Chen, Jianteng Liu, Jingyi Liang, Qiuyin Qin, Weixu Qi, Liang Chen, Jia Li, Bo Li, Xidong Duan
{"title":"Synthesis, Modulation, and Application of Two-Dimensional TMD Heterostructures.","authors":"Ruixia Wu, Hongmei Zhang, Huifang Ma, Bei Zhao, Wei Li, Yang Chen, Jianteng Liu, Jingyi Liang, Qiuyin Qin, Weixu Qi, Liang Chen, Jia Li, Bo Li, Xidong Duan","doi":"10.1021/acs.chemrev.4c00174","DOIUrl":"10.1021/acs.chemrev.4c00174","url":null,"abstract":"<p><p>Two-dimensional (2D) transition metal dichalcogenide (TMD) heterostructures have attracted a lot of attention due to their rich material diversity and stack geometry, precise controllability of structure and properties, and potential practical applications. These heterostructures not only overcome the inherent limitations of individual materials but also enable the realization of new properties through appropriate combinations, establishing a platform to explore new physical and chemical properties at micro-nano-pico scales. In this review, we systematically summarize the latest research progress in the synthesis, modulation, and application of 2D TMD heterostructures. We first introduce the latest techniques for fabricating 2D TMD heterostructures, examining the rationale, mechanisms, advantages, and disadvantages of each strategy. Furthermore, we emphasize the importance of characteristic modulation in 2D TMD heterostructures and discuss some approaches to achieve novel functionalities. Then, we summarize the representative applications of 2D TMD heterostructures. Finally, we highlight the challenges and future perspectives in the synthesis and device fabrication of 2D TMD heterostructures and provide some feasible solutions.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"10112-10191"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142071286","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-06DOI: 10.1021/acs.chemrev.4c00105
Mikkel Bregnhøj, Frederik Thorning, Peter R Ogilby
{"title":"Singlet Oxygen Photophysics: From Liquid Solvents to Mammalian Cells.","authors":"Mikkel Bregnhøj, Frederik Thorning, Peter R Ogilby","doi":"10.1021/acs.chemrev.4c00105","DOIUrl":"10.1021/acs.chemrev.4c00105","url":null,"abstract":"<p><p>Molecular oxygen, O<sub>2</sub>, has long provided a cornerstone for studies in chemistry, physics, and biology. Although the triplet ground state, O<sub>2</sub>(X<sup>3</sup>Σ<sub>g</sub><sup>-</sup>), has garnered much attention, the lowest excited electronic state, O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>), commonly called singlet oxygen, has attracted appreciable interest, principally because of its unique chemical reactivity in systems ranging from the Earth's atmosphere to biological cells. Because O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) can be produced and deactivated in processes that involve light, the photophysics of O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) are equally important. Moreover, pathways for O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) deactivation that regenerate O<sub>2</sub>(X<sup>3</sup>Σ<sub>g</sub><sup>-</sup>), which address fundamental principles unto themselves, kinetically compete with the chemical reactions of O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) and, thus, have practical significance. Due to technological advances (e.g., lasers, optical detectors, microscopes), data acquired in the past ∼20 years have increased our understanding of O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) photophysics appreciably and facilitated both spatial and temporal control over the behavior of O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>). One goal of this Review is to summarize recent developments that have broad ramifications, focusing on systems in which oxygen forms a contact complex with an organic molecule M (e.g., a liquid solvent). An important concept is the role played by the M<sup>+•</sup>O<sub>2</sub><sup>-•</sup> charge-transfer state in both the formation and deactivation of O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>).</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"9949-10051"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141892264","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11DOI: 10.1021/acs.chemrev.4c00211
Paul A. Kempler, Robert H. Coridan, Long Luo
{"title":"Gas Evolution in Water Electrolysis","authors":"Paul A. Kempler, Robert H. Coridan, Long Luo","doi":"10.1021/acs.chemrev.4c00211","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00211","url":null,"abstract":"Gas bubbles generated by the hydrogen evolution reaction and oxygen evolution reaction during water electrolysis influence the energy conversion efficiency of hydrogen production. Here, we survey what is known about the interaction of gas bubbles and electrode surfaces and the influence of gas evolution on practicable devices used for water electrolysis. We outline the physical processes occurring during the life cycle of a bubble, summarize techniques used to characterize gas evolution phenomena in situ and in practical device environments, and discuss ways that electrodes can be tailored to facilitate gas removal at high current densities. Lastly, we review efforts to model the behavior of individual gas bubbles and multiphase flows produced at gas-evolving electrodes. We conclude our review with a short summary of outstanding questions that could be answered by future efforts to characterize gas evolution in electrochemical device environments or by improved simulations of multiphase flows.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"17 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142171360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-12DOI: 10.1021/acs.chemrev.3c00851
Guodong Xue, Biao Qin, Chaojie Ma, Peng Yin, Can Liu, Kaihui Liu
{"title":"Large-Area Epitaxial Growth of Transition Metal Dichalcogenides.","authors":"Guodong Xue, Biao Qin, Chaojie Ma, Peng Yin, Can Liu, Kaihui Liu","doi":"10.1021/acs.chemrev.3c00851","DOIUrl":"10.1021/acs.chemrev.3c00851","url":null,"abstract":"<p><p>Over the past decade, research on atomically thin two-dimensional (2D) transition metal dichalcogenides (TMDs) has expanded rapidly due to their unique properties such as high carrier mobility, significant excitonic effects, and strong spin-orbit couplings. Considerable attention from both scientific and industrial communities has fully fueled the exploration of TMDs toward practical applications. Proposed scenarios, such as ultrascaled transistors, on-chip photonics, flexible optoelectronics, and efficient electrocatalysis, critically depend on the scalable production of large-area TMD films. Correspondingly, substantial efforts have been devoted to refining the synthesizing methodology of 2D TMDs, which brought the field to a stage that necessitates a comprehensive summary. In this Review, we give a systematic overview of the basic designs and significant advancements in large-area epitaxial growth of TMDs. We first sketch out their fundamental structures and diverse properties. Subsequent discussion encompasses the state-of-the-art wafer-scale production designs, single-crystal epitaxial strategies, and techniques for structure modification and postprocessing. Additionally, we highlight the future directions for application-driven material fabrication and persistent challenges, aiming to inspire ongoing exploration along a revolution in the modern semiconductor industry.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"9785-9865"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141915427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-09-11Epub Date: 2024-08-28DOI: 10.1021/acs.chemrev.4c00157
Lenan Zhang, Ryuichi Iwata, Zhengmao Lu, Xuanjie Wang, Carlos D Díaz-Marín, Yang Zhong
{"title":"Bridging Innovations of Phase Change Heat Transfer to Electrochemical Gas Evolution Reactions.","authors":"Lenan Zhang, Ryuichi Iwata, Zhengmao Lu, Xuanjie Wang, Carlos D Díaz-Marín, Yang Zhong","doi":"10.1021/acs.chemrev.4c00157","DOIUrl":"10.1021/acs.chemrev.4c00157","url":null,"abstract":"<p><p>Bubbles play a ubiquitous role in electrochemical gas evolution reactions. However, a mechanistic understanding of how bubbles affect the energy efficiency of electrochemical processes remains limited to date, impeding effective approaches to further boost the performance of gas evolution systems. From a perspective of the analogy between heat and mass transfer, bubbles in electrochemical gas evolution reactions exhibit highly similar dynamic behaviors to them in the liquid-vapor phase change. Recent developments of liquid-vapor phase change systems have substantially advanced the fundamental knowledge of bubbles, leading to unprecedented enhancement of heat transfer performance. In this Review, we aim to elucidate a promising opportunity of understanding bubble dynamics in electrochemical gas evolution reactions through a lens of phase change heat transfer. We first provide a background about key parallels between electrochemical gas evolution reactions and phase change heat transfer. Then, we discuss bubble dynamics in gas evolution systems across multiple length scales, with an emphasis on exciting research problems inspired by new insights gained from liquid-vapor phase change systems. Lastly, we review advances in engineered surfaces for manipulating bubbles to enhance heat and mass transfer, providing an outlook on the design of high-performance gas evolving electrodes.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"10052-10111"},"PeriodicalIF":51.4,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142078411","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-08-30DOI: 10.1021/acs.chemrev.3c00951
Annalisa Pierro, Alessio Bonucci, Axel Magalon, Valérie Belle, Elisabetta Mileo
{"title":"Impact of Cellular Crowding on Protein Structural Dynamics Investigated by EPR Spectroscopy","authors":"Annalisa Pierro, Alessio Bonucci, Axel Magalon, Valérie Belle, Elisabetta Mileo","doi":"10.1021/acs.chemrev.3c00951","DOIUrl":"https://doi.org/10.1021/acs.chemrev.3c00951","url":null,"abstract":"The study of how the intracellular medium influences protein structural dynamics and protein–protein interactions is a captivating area of research for scientists aiming to comprehend biomolecules in their native environment. As the cellular environment can hardly be reproduced <i>in vitro</i>, direct investigation of biomolecules within cells has attracted growing interest in the past two decades. Among magnetic resonances, site-directed spin labeling coupled to electron paramagnetic resonance spectroscopy (SDSL-EPR) has emerged as a powerful tool for studying the structural properties of biomolecules directly in cells. Since the first <i>in-cell</i> EPR experiment was reported in 2010, substantial progress has been made, and this Review provides a detailed overview of the developments and applications of this spectroscopic technique. The strategies available for preparing a cellular sample and the EPR methods that can be applied to cells will be discussed. The array of spin labels available, along with their strengths and weaknesses in cellular contexts, will also be described. Several examples will illustrate how <i>in-cell</i> EPR can be applied to different biological systems and how the cellular environment affects the structural and dynamic properties of different proteins. Lastly, the Review will focus on the future developments expected to expand the capabilities of this promising technique.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"52 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}