Chemical Reviews最新文献_第3页

Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

IF 51.4 1区化学

Chemical Reviews Pub Date : 2025-03-07 DOI: 10.1021/acs.chemrev.4c0080810.1021/acs.chemrev.4c00808

Toshifumi Dohi*, Elghareeb E. Elboray, Kotaro Kikushima, Koji Morimoto and Yasuyuki Kita*,

{"title":"Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations","authors":"Toshifumi Dohi*, Elghareeb E. Elboray, Kotaro Kikushima, Koji Morimoto and Yasuyuki Kita*, ","doi":"10.1021/acs.chemrev.4c0080810.1021/acs.chemrev.4c00808","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00808https://doi.org/10.1021/acs.chemrev.4c00808","url":null,"abstract":"Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl–halide bonds is a crucial step of most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling the direct (hetero)arylation of trapping reagents and construction of highly functionalized (hetero)arenes under benign conditions. The strategies for the activation of aryl iodides are classified into (a) hypervalent iodoarene activation followed by functionalization under thermal/photochemical conditions, (b) aryl–I bond dissociation in the presence of bases with/without organic catalysts and promoters, (c) photoinduced aryl–I bond dissociation in the presence/absence of organophotocatalysts, (d) electrochemical activation of aryl iodides by direct/indirect electrolysis mediated by organocatalysts and mediators acting as electron shuttles, and (e) electrophotochemical activation of aryl iodides mediated by redox-active organocatalysts. These activation modes result in aryl iodides exhibiting diverse reactivity as formal aryl cations/radicals/anions and aryne precursors. The coupling of these reactive intermediates with trapping reagents leads to the facile and selective formation of C–C and C–heteroatom bonds. These ecofriendly, inexpensive, and functional group-tolerant activation strategies offer green alternatives to transition metal-based catalysis.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"125 6","pages":"3440–3550 3440–3550"},"PeriodicalIF":51.4,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.chemrev.4c00808","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696572","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}

引用次数: 0

Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

IF 62.1 1区化学

Chemical Reviews Pub Date : 2025-03-07 DOI: 10.1021/acs.chemrev.4c00808

Toshifumi Dohi, Elghareeb E. Elboray, Kotaro Kikushima, Koji Morimoto, Yasuyuki Kita

{"title":"Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations","authors":"Toshifumi Dohi, Elghareeb E. Elboray, Kotaro Kikushima, Koji Morimoto, Yasuyuki Kita","doi":"10.1021/acs.chemrev.4c00808","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00808","url":null,"abstract":"Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl–halide bonds is a crucial step of most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling the direct (hetero)arylation of trapping reagents and construction of highly functionalized (hetero)arenes under benign conditions. The strategies for the activation of aryl iodides are classified into (a) hypervalent iodoarene activation followed by functionalization under thermal/photochemical conditions, (b) aryl–I bond dissociation in the presence of bases with/without organic catalysts and promoters, (c) photoinduced aryl–I bond dissociation in the presence/absence of organophotocatalysts, (d) electrochemical activation of aryl iodides by direct/indirect electrolysis mediated by organocatalysts and mediators acting as electron shuttles, and (e) electrophotochemical activation of aryl iodides mediated by redox-active organocatalysts. These activation modes result in aryl iodides exhibiting diverse reactivity as formal aryl cations/radicals/anions and aryne precursors. The coupling of these reactive intermediates with trapping reagents leads to the facile and selective formation of C–C and C–heteroatom bonds. These ecofriendly, inexpensive, and functional group-tolerant activation strategies offer green alternatives to transition metal-based catalysis.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"17 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570074","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}

引用次数: 0

Non-Nernstian Effects in Theoretical Electrocatalysis

IF 62.1 1区化学

Chemical Reviews Pub Date : 2025-03-06 DOI: 10.1021/acs.chemrev.4c00803

Dipam Manish Patel, Georg Kastlunger

引用次数: 0

Advances in the Synthesis of Cyclopropylamines

IF 62.1 1区化学

Chemical Reviews Pub Date : 2025-03-06 DOI: 10.1021/acs.chemrev.4c00674

Philippe Bertus, Julien Caillé

{"title":"Advances in the Synthesis of Cyclopropylamines","authors":"Philippe Bertus, Julien Caillé","doi":"10.1021/acs.chemrev.4c00674","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00674","url":null,"abstract":"Cyclopropylamines are an important subclass of substituted cyclopropanes that combine the unique electronic and steric properties of cyclopropanes with the presence of a donor nitrogen atom. In addition to their presence in a diverse array of biologically active compounds, cyclopropylamines are utilized as important synthetic intermediates, particularly in ring-opening or cycloaddition reactions. Consequently, the synthesis of these compounds has constituted a significant research topic, as evidenced by the abundant published synthetic methods. In addition to the widely used Curtius rearrangement, classical cyclopropanation methods have been adapted to integrate a nitrogen function (Simmons–Smith reaction, metal-catalyzed reaction of diazo compounds on olefins, Michael-initiated ring-closure reactions) with significant advances in enantioselective synthesis. More recently, specific methods have been developed for the preparation of the aminocyclopropane moiety (Kulinkovich reactions applied to amides and nitriles, addition to cyclopropenes, metal-catalyzed reactions involving C–H functionalization, ...). The topic of this review is to present the different methods for the preparation of cyclopropylamine derivatives, with the aim of covering the methodological advances as best as possible, highlighting their scope, their stereochemical aspects and future trends.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"18 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570075","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}

引用次数: 0

Non-Nernstian Effects in Theoretical Electrocatalysis

IF 51.4 1区化学

Chemical Reviews Pub Date : 2025-03-06 DOI: 10.1021/acs.chemrev.4c0080310.1021/acs.chemrev.4c00803

Dipam Manish Patel, and , Georg Kastlunger*,

{"title":"Non-Nernstian Effects in Theoretical Electrocatalysis","authors":"Dipam Manish Patel,  and , Georg Kastlunger*, ","doi":"10.1021/acs.chemrev.4c0080310.1021/acs.chemrev.4c00803","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00803https://doi.org/10.1021/acs.chemrev.4c00803","url":null,"abstract":"Electrocatalysis is one of the principal pathways for the transition to sustainable chemistry, promising greater energy efficiency and reduced emissions. As the field has grown, our theoretical understanding has matured. The influence of the applied potential on reactivity has developed from the first-order predictions based on the Nernst equation to the implicit inclusion of second-order effects including the interaction of reacting species with the interfacial electric field. In this review, we explore these non-Nernstian field effects in electrocatalysis, aiming to both understand and exploit them through theory and computation. We summarize the critical distinction between Nernstian and non-Nernstian effects and outline strategies to address the latter in theoretical studies. Subsequently, we examine the specific energetic contributions of the latter on capacitive and faradaic processes separately. We also underscore the importance of considering non-Nernstian effects in catalyst screening and mechanistic analysis. Finally, we provide suggestions on how to experimentally unravel these effects, offering insights into practical approaches for advancing the field.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"125 6","pages":"3378–3400 3378–3400"},"PeriodicalIF":51.4,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696571","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}

引用次数: 0

Advances in the Synthesis of Cyclopropylamines

IF 51.4 1区化学

Chemical Reviews Pub Date : 2025-03-06 DOI: 10.1021/acs.chemrev.4c0067410.1021/acs.chemrev.4c00674

Philippe Bertus*, and , Julien Caillé,

{"title":"Advances in the Synthesis of Cyclopropylamines","authors":"Philippe Bertus*,  and , Julien Caillé, ","doi":"10.1021/acs.chemrev.4c0067410.1021/acs.chemrev.4c00674","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00674https://doi.org/10.1021/acs.chemrev.4c00674","url":null,"abstract":"Cyclopropylamines are an important subclass of substituted cyclopropanes that combine the unique electronic and steric properties of cyclopropanes with the presence of a donor nitrogen atom. In addition to their presence in a diverse array of biologically active compounds, cyclopropylamines are utilized as important synthetic intermediates, particularly in ring-opening or cycloaddition reactions. Consequently, the synthesis of these compounds has constituted a significant research topic, as evidenced by the abundant published synthetic methods. In addition to the widely used Curtius rearrangement, classical cyclopropanation methods have been adapted to integrate a nitrogen function (Simmons–Smith reaction, metal-catalyzed reaction of diazo compounds on olefins, Michael-initiated ring-closure reactions) with significant advances in enantioselective synthesis. More recently, specific methods have been developed for the preparation of the aminocyclopropane moiety (Kulinkovich reactions applied to amides and nitriles, addition to cyclopropenes, metal-catalyzed reactions involving C–H functionalization, ...). The topic of this review is to present the different methods for the preparation of cyclopropylamine derivatives, with the aim of covering the methodological advances as best as possible, highlighting their scope, their stereochemical aspects and future trends.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"125 6","pages":"3242–3377 3242–3377"},"PeriodicalIF":51.4,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696569","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}

引用次数: 0

Drugging Challenging Cancer Targets Using Fragment-Based Methods

IF 62.1 1区化学

Chemical Reviews Pub Date : 2025-03-05 DOI: 10.1021/acs.chemrev.4c00892

Stephen W. Fesik

引用次数: 0

Drugging Challenging Cancer Targets Using Fragment-Based Methods

IF 51.4 1区化学

Chemical Reviews Pub Date : 2025-03-05 DOI: 10.1021/acs.chemrev.4c0089210.1021/acs.chemrev.4c00892

Stephen W. Fesik*,

引用次数: 0

Connecting the Dots: Sintering of Liquid Metal Particles for Soft and Stretchable Conductors

IF 62.1 1区化学

Chemical Reviews Pub Date : 2025-03-04 DOI: 10.1021/acs.chemrev.4c00850

Simok Lee, Syed Ahmed Jaseem, Nurit Atar, Meixiang Wang, Jeong Yong Kim, Mohammadreza Zare, Sooyoung Kim, Michael D. Bartlett, Jae-Woong Jeong, Michael D. Dickey

引用次数: 0

Connecting the Dots: Sintering of Liquid Metal Particles for Soft and Stretchable Conductors

IF 51.4 1区化学

Chemical Reviews Pub Date : 2025-03-04 DOI: 10.1021/acs.chemrev.4c0085010.1021/acs.chemrev.4c00850

Simok Lee, Syed Ahmed Jaseem, Nurit Atar, Meixiang Wang, Jeong Yong Kim, Mohammadreza Zare, Sooyoung Kim, Michael D. Bartlett, Jae-Woong Jeong and Michael D. Dickey*,

{"title":"Connecting the Dots: Sintering of Liquid Metal Particles for Soft and Stretchable Conductors","authors":"Simok Lee, Syed Ahmed Jaseem, Nurit Atar, Meixiang Wang, Jeong Yong Kim, Mohammadreza Zare, Sooyoung Kim, Michael D. Bartlett, Jae-Woong Jeong and Michael D. Dickey*, ","doi":"10.1021/acs.chemrev.4c0085010.1021/acs.chemrev.4c00850","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00850https://doi.org/10.1021/acs.chemrev.4c00850","url":null,"abstract":"This review focuses on the sintering of liquid metal particles (LMPs). Here, sintering means the partial merging or connecting of particles (or droplets) to form a network of percolated and, thus, conductive electrical pathways. LMPs are attractive materials because they can be suspended in a carrier fluid to create printable inks or distributed in an elastomer to create soft, stretchable composites. However, films and traces of LMPs are not typically conductive as fabricated due to the native oxide that forms on the surface of the particles. In the case of composites, polymers can also get between particles, making sintering more challenging. Sintering can be done via a variety of ways, such as mechanical, thermal, and chemical processing. This review discusses the mechanisms to sinter these particles, patterning techniques that use sintering, unique properties of sintered LMPs, and their practical applications in fields such as stretchable electronics, soft robotics, and active materials.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"125 6","pages":"3551–3585 3551–3585"},"PeriodicalIF":51.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696566","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}

引用次数: 0