{"title":"Photoredox/Ti dual-catalyzed dehydroxylative ring-opening Giese reaction of cyclobutanone oximes","authors":"","doi":"10.1016/j.gresc.2023.04.005","DOIUrl":"10.1016/j.gresc.2023.04.005","url":null,"abstract":"<div><p>A dehydroxylative ring-opening Giese reaction of cyclobutanone oximes enabled by photoredox/Ti dual catalysis has been reported in this work. This protocol avoids the prefunctionalization of oximes and the use of stoichiometric triarylphosphine reagents. It also features mild conditions, broad substrate scope and good functional group tolerance. The gram-scale reaction, product derivatization, late-stage functionalization of complex pharmaceutical and natural product derivatives, and oligopeptide modification exhibit the potential application of this methodology in synthetic chemistry.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 159-164"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000340/pdfft?md5=aef33f37abbf723bb234b027851d013f&pid=1-s2.0-S2666554923000340-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90946731","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A sustainable synthesis of 3,3-disubstituted oxindoles via CuBr-catalysed capture of carboxylic oxonium ylides with isatylidene malononitrile","authors":"","doi":"10.1016/j.gresc.2023.04.006","DOIUrl":"10.1016/j.gresc.2023.04.006","url":null,"abstract":"<div><p>We herein reported a sustainable synthesis of 3,3-disubstituted oxindoles <em>via</em> a Michael-type reaction based on the CuBr-catalysed capture of carboxylic oxonium ylides with isatylidene malononitrile. The reaction is characterized by a high atom economy and low economic constraints. The catalyst CuBr could be conveniently recyclized. The products of the reaction were found to be inhibitory against Na ion channels. We expect the reaction to shed the light on synthesis of biologically interesting molecules directed by principles of green chemistry.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 180-185"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000352/pdfft?md5=7da1e0d79a36caa2953b126886141822&pid=1-s2.0-S2666554923000352-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91482742","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Copper-catalyzed 2,3-dihydro-1,2,4-triazoles synthesis through [3+2]-cycloaddition of nitrile ylides with azodicarboxylates","authors":"","doi":"10.1016/j.gresc.2023.01.007","DOIUrl":"10.1016/j.gresc.2023.01.007","url":null,"abstract":"<div><p>A copper-catalyzed three-component reaction of diazo compounds, nitriles, and azodicarboxylates to construct 2,3-dihydro-1,2,4-triazoles is reported. Key to the success is the utilization of azodicarboxylates to trap the <em>in-situ</em> formed nitrile ylides from diazo compounds by [3 + 2]-cycloaddition. Both the acceptor-only and donor-acceptor diazo compounds are all tolerated to the strategy. The synthetic value of this protocol is illustrated by gram-scale synthesis and valuable transformation of the obtained 2,3-dihydro-1,2,4-triazoles.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 191-194"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000078/pdfft?md5=8ffdf7f585f2ecff517fe96703f127a2&pid=1-s2.0-S2666554923000078-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79373283","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of highly functional quinazolins via metal-free, visible-light-enabled radical cascade arylation/cyclization of fluorinated imidoyl isothiocyanates","authors":"","doi":"10.1016/j.gresc.2023.07.003","DOIUrl":"10.1016/j.gresc.2023.07.003","url":null,"abstract":"<div><p>A metal-free, efficient and easy-to-hand protocol for the synthesis of 2-perfluoroalkylquinazolins has been achieved by Eosin B catalyzed radical cascade arylation/cyclization reaction of fluorinated imidoyl isothiocyanates with aryldiazonium Salts. A variety of highly functionalized quinozaline derivatives bearing pharmaceutically important thiol and fluoroalkyl groups were efficiently assembled with broad substrate scope and good functional group tolerance. A series of mechanism experiments indicate that this reaction undergoes a radical cascade arylation/cyclization pathway.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 200-204"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S266655492300056X/pdfft?md5=7ddaf54cf1fae5ff3cb51c49da7dfef5&pid=1-s2.0-S266655492300056X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85837929","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Metal-free and water-compatible nanocatalysts for green photocatalytic dehydrogenation in aqueous medium","authors":"","doi":"10.1016/j.gresc.2023.03.001","DOIUrl":"10.1016/j.gresc.2023.03.001","url":null,"abstract":"<div><p>Two types of poly-porphyrin-based heterogeneous photocatalysts including insoluble polymer and water-soluble nanoparticles exhibited excellent photocatalytic activity in visible-light-induced dehydrogenation in water. The extremely low catalyst loading (0.01 mol%) of water-soluble nanoparticles provided so far the highest turnover frequency (TOF) value (333 h<sup>-1</sup>) for such transformation among reported records.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 186-190"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000285/pdfft?md5=8ebe2be535bad39e84ce35d0ab7ac238&pid=1-s2.0-S2666554923000285-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86932884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Pd(II)/N,N′-Disulfonyl bisimidazoline-catalyzed asymmetric arylation of isoquinoline-1,3,4-trione-derived ketimines","authors":"","doi":"10.1016/j.gresc.2023.07.001","DOIUrl":"10.1016/j.gresc.2023.07.001","url":null,"abstract":"<div><p>A palladium/chiral <em>N</em>,<em>N</em>′-disulfonyl bisimidazoline (Bim)-catalyzed asymmetric addition of arylboronic acids to isoquinoline-1,3,4-trione-derived ketimines is reported, leading to the generation of a series of functionalized isoquinoline-1,3(2<em>H</em>,4<em>H</em>)-diones bearing one quaternary carbon-amino functionality in good to excellent yields with ≥95% <em>ee</em> in most cases. The reaction has remarkable compatibility with both substrate scopes, providing a highly enantioselective entry to chiral heterocyclic α-tertiary amines.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 165-169"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000546/pdfft?md5=3d515c77b647776f96377b97b7fd7c8f&pid=1-s2.0-S2666554923000546-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89921621","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A H2O2 generation-detection-regulation integrated platform for boosting the efficiency of peroxygenase-catalysed C–H oxidative hydroxylation","authors":"","doi":"10.1016/j.gresc.2023.11.006","DOIUrl":"10.1016/j.gresc.2023.11.006","url":null,"abstract":"<div><p>The peroxygenases are ideal biocatalysts for the selective oxyfunctionalisation of stable C–H bonds. However, the catalytic efficiency of this approach is limited due to enzyme lability toward oxidant H<sub>2</sub>O<sub>2</sub>. Although the reported <em>in-situ</em> H<sub>2</sub>O<sub>2</sub> generation system enables the stable biocatalytic process without deactivating the enzyme, the greatest catalytic potential of peroxygenases still cannot be fulfilled effectively. To address the above issue, a H<sub>2</sub>O<sub>2</sub> generation-detection-regulation platform that integrated an effective organocatalyst-driven H<sub>2</sub>O<sub>2</sub> generation system, a precise electrochemical H<sub>2</sub>O<sub>2</sub> real-time detection device, and a convenient H<sub>2</sub>O<sub>2</sub> regulation strategy was first developed. The suitable range of H<sub>2</sub>O<sub>2</sub> generation rate for maximizing the catalytic efficiency of peroxygenases while minimizing inactivation of the enzyme was firstly obtained by simply adjusting the amount of organocatalyst. According to the determined suitable range, the C–H oxyfunctionalisation efficiency of peroxygenases for each substrate was significantly boosted, achieving ∼3-fold of the reported highest turnover frequency.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 153-158"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S266655492300100X/pdfft?md5=1ac9958ba7a3d4adcfa9a5a865502f1e&pid=1-s2.0-S266655492300100X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512293","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Ate complexes in organic synthesis: From ate reagents to ate catalysts","authors":"","doi":"10.1016/j.gresc.2024.04.010","DOIUrl":"10.1016/j.gresc.2024.04.010","url":null,"abstract":"<div><p>The realm of application of organometallic catalysis to organic synthesis has witnessed a transformative shift in recent years, owing much to the evolution of ate complexes from mere reagents to versatile catalysts. Ate complexes, formed through the coordination of a neutral Lewis acid with an organic anionic base, have emerged as pivotal intermediates that not only facilitate organic transformations but also serve as efficient catalysts in a wide range of chemical reactions. This review presents the fascinating journey of ate complexes, highlighting their development from stoichiometric reagents to active catalysts. Historically, ate complexes were primarily regarded as stoichiometric species essential for various metal-catalyzed transformations. However, constant research has unveiled their potential as catalysts in their own right, reshaping the landscape of modern organic synthesis. In this minireview, we discuss the pivotal role of ate complexes in the evolution of organic synthesis, from their early days as reactive intermediates to their current stature as catalytic pioneers offering a glimpse into the exciting future of this dynamic field.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 141-152"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S266655492400053X/pdfft?md5=7a4de4c94a8dbec8c809e1e05e1cb03f&pid=1-s2.0-S266655492400053X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141037151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of 1,4-oxathiins via [3+3] annulation of pyridinium 1,4‐zwitterionic thiolates with iodonium ylides","authors":"Zhibin Niu, C. Pi, Yangjie Wu, Xiuling Cui","doi":"10.1016/j.gresc.2024.07.002","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.07.002","url":null,"abstract":"","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"12 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141848730","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}