{"title":"Rhodium/Ming-Phos-catalyzed asymmetric annulation reaction of silacyclobutanes with terminal alkynes","authors":"","doi":"10.1016/j.gresc.2023.09.001","DOIUrl":"10.1016/j.gresc.2023.09.001","url":null,"abstract":"<div><p>Asymmetric ring-expansion reactions of silacyclobutanes (SCBs) with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds. However, the achievement of highly enantioselective annulation of SCBs with terminal alkynes remains a challenge. Herein, we report a rhodium-catalyzed asymmetric annulation reaction of SCBs with terminal alkynes, which relies on the newly identified chiral sulfinamide phosphine ligand Ming-Phos. This catalytic system exhibits unique effects under mild conditions, leading to the direct synthesis of structurally diverse chiral silacycles in moderate to good yields with high enantioselectivities (up to 95% <em>ee</em>).</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 205-210"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000765/pdfft?md5=284277fb8ad4ace21d9486ab6435b6da&pid=1-s2.0-S2666554923000765-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91134538","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":"N-Doped graphene fiber anchored Pd nanoparticles as a fixed-bed catalyst for continuous-flow reduction of N-containing unsaturated compounds","authors":"","doi":"10.1016/j.gresc.2023.08.003","DOIUrl":"10.1016/j.gresc.2023.08.003","url":null,"abstract":"<div><p>Catalytic fixed-bed is an efficient and facile system for scalable organic synthesis due to its continuous and fast flow operation process. As a key unit in the fixed-bed system, catalytically active packing materials are required to possess some properties, such as high activity, excellent stability, and porous packing structure. Herein, we prepare a fibrous fixed-bed catalyst by anchoring Pd nanoparticles on <em>N</em>-doped graphene fiber (NHG) (Pd/NGF). Due to the porous and loose packing structure, the resultant Pd/NGF catalyst can be easily filled into the continuous-flow reactor to construct a fixed-bed system with low flow resistance. The corresponding catalytic fixed-bed system exhibits a favourable flow rate (8 mL/min) and excellent durability toward reduction reactions of <em>N</em>-containing unsaturated compounds to produce aromatic amines. This work provides a new design concept of fibrous fixed-bed catalysts with dual-active components (<em>i.e.</em>, graphene-derived active materials and metal nanoparticles) and catalytic organic synthesis in a continuous-flow process.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 170-174"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000741/pdfft?md5=bfbae0b4e0dfc79e63a1e9f1e68b9fec&pid=1-s2.0-S2666554923000741-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135248384","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":"Iridium-Catalyzed asymmetric reduction of α,β-Unsaturated nitriles with water","authors":"","doi":"10.1016/j.gresc.2023.07.002","DOIUrl":"10.1016/j.gresc.2023.07.002","url":null,"abstract":"<div><p>The nitrile compounds are present in a variety of biologically active natural products and pharmaceuticals, and the nitrile groups are versatile synthetic intermediates to other functionalized compounds. Herein, the asymmetric reduction of <em>α,</em> <em>β</em>-unsaturated nitriles with water as a hydrogen source is reported. The reaction is catalyzed by the complex of [Ir(COD)Cl]<sub>2</sub> and (<em>R</em><sub>a</sub>, <em>S</em>)-Ph-Bn-SiPhox, and allows the preparation of useful enantioenriched chiral 3,3-disubstituted propionitriles with high optical purities in mild conditions.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 175-179"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000558/pdfft?md5=929630f8326071a3d9469b577f890d6c&pid=1-s2.0-S2666554923000558-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80594047","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- and light-free approach to polyheterocycles via a quinone-Cs2CO3 couple promoted regioselective cascade radical cyclization","authors":"","doi":"10.1016/j.gresc.2023.04.001","DOIUrl":"10.1016/j.gresc.2023.04.001","url":null,"abstract":"<div><p>A highly efficient, transition-metal- and light-free approach to polyheterocycles <em>via</em> regioselective cascade radical cyclization is developed. The redox-neutral protocol has a broad substrate scope with good functional group tolerance and probably undergoes a <em>SET</em> process, which is initiated by catalytic amounts of quinone in combination with 2.0 equiv. of Cs<sub>2</sub>CO<sub>3</sub>.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 3","pages":"Pages 195-199"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000303/pdfft?md5=70471b3c5a6b774bf02c852c0e47facf&pid=1-s2.0-S2666554923000303-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76274831","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":"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}