Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling
{"title":"Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines","authors":"Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling","doi":"10.1016/j.gresc.2023.11.008","DOIUrl":"10.1016/j.gresc.2023.11.008","url":null,"abstract":"<div><div>Herein, we reported an efficient and straightforward method to realize desaturated <em>β</em>-C(sp<sup>3</sup>)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP<sub>2</sub>Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 297-302"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512304","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}
Wanjun Chen , Xinlong Yan , Lin Fan , Xu Guo , Jian Yang , Yiming Chen , Shaofang Zhou , Guodu Liu
{"title":"Highly enantio-stereoselective Ni-catalyzed reductive cyclization to cyclopentanes with chiral quaternary centres of trisubstituted allylic siloxanes","authors":"Wanjun Chen , Xinlong Yan , Lin Fan , Xu Guo , Jian Yang , Yiming Chen , Shaofang Zhou , Guodu Liu","doi":"10.1016/j.gresc.2023.08.004","DOIUrl":"10.1016/j.gresc.2023.08.004","url":null,"abstract":"<div><div>The construction of chiral quaternary carbon stereocenters is a significant challenge in asymmetric synthesis. Catalytic synthesis of these structures with trisubstituted allylic alcohols is highly important. However, most of the reported methodologies required noble transition-metals. Herein we reported the first highly asymmetric stereoselective synthesis of cyclopentanes bearing chiral quaternary carbon stereocenters of trisubstituted allylic siloxanes by reductive cyclization of all carbon 1,6-alkynones with the non-noble nickel catalysis of Ni(cod)<sub>2</sub> with <em>P</em>-chiral monophosphine ligand <strong>(<em>S</em>)-BIDIME</strong>. Various multi-substituted functionalized cyclopentanes were obtained in high yields (up to 96%), excellent enantioselectivities (up to >99% <em>ee</em>) and perfect stereoselectivities (>99:1 <em>E/Z</em>). Thirty-two examples were successfully established for this method. Clarified mechanism studies were investigated first time by React-IR and DFT calculations to understand and explain the ligand-control of excellent enantio-stereoselectivity. Gram-scale reaction and control experiments were carried out. A new reaction design was proposed for further application of this type of catalysis.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 282-289"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89588262","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}
Chao Xu , Yingkun Luo , Shengtong Niu , Fan Gong , Shouang Lan , Benlong Luo , Jinggong Liu , Shuang Yang , Xinqiang Fang
{"title":"Transition-metal and base-free ether synthesis via alcohol-participated yne-allylic substitution","authors":"Chao Xu , Yingkun Luo , Shengtong Niu , Fan Gong , Shouang Lan , Benlong Luo , Jinggong Liu , Shuang Yang , Xinqiang Fang","doi":"10.1016/j.gresc.2023.10.003","DOIUrl":"10.1016/j.gresc.2023.10.003","url":null,"abstract":"<div><div>Ethers are among the most important chemicals in organic synthesis, the pharmaceutical industry, agrochemical production, and material science. C–O bond formation via substitution is one of the most widely used strategies for ether formation. However, known methods usually employ transition-metal and bases to facilitate the process. In this work, we describe the base- and transition-metal-free ether formation <em>via</em> alcohol and phenol-participated substitution. The protocol allows access to a large number of ethers with enyne functional moieties, and features mild reaction conditions, high efficiency, and good regio- and stereoselectivities. The reaction could be readily scaled up, and the products could be used in a range of further transformations.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 303-309"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136010199","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}
Jingjing Wang , Feng Li , Kai Liu , Chong Li , Sheng Cao , Yuxiang Wu , Yongjun Yuan , Fei Teng , Teng Wang , Yao Zhou
{"title":"Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines","authors":"Jingjing Wang , Feng Li , Kai Liu , Chong Li , Sheng Cao , Yuxiang Wu , Yongjun Yuan , Fei Teng , Teng Wang , Yao Zhou","doi":"10.1016/j.gresc.2023.10.002","DOIUrl":"10.1016/j.gresc.2023.10.002","url":null,"abstract":"<div><div>We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. The mechanistic study revealed a radical process. In addition, the usefulness of the reaction in organic synthesis was proved by the scale-up synthesis as well as the late-stage modification of drug-like molecules.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 315-318"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135852345","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}
Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang
{"title":"Transition metal-free Csp3-Csp3 bond-forming reactions of N-tosylaziridines and gem-diborylalkanes","authors":"Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang","doi":"10.1016/j.gresc.2023.07.004","DOIUrl":"10.1016/j.gresc.2023.07.004","url":null,"abstract":"<div><div>The incorporation of additional Csp<sup>3</sup> atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp<sup>3</sup>-Csp<sup>3</sup> bonds efficiently and practically. The present article reports a novel Csp<sup>3</sup>-Csp<sup>3</sup> bond-forming reaction of 2-aryl/alkyl substituted aziridines with <em>gem</em>-diborylalkanes under tranisiton metal free conditions. A wide range of <em>γ</em>-<em>gem</em>-diboronate esters substituted amines can be accessed in good yield and regioselectivity. The results demonstrated that various aziridines could react with <em>gem</em>-diborylalkanes in the presence of LiTMP as the base within 15 min at ambient temperature.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 329-333"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"123572670","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":"Photocatalytic selective 1,4-oxyimination/diamination across C=C and N=N bonds to access structurally diverse N-N-N triazane derivatives","authors":"Yu-Shi Jiang, Dan-Na Chen, Huan Jiang, Peng-Ju Xia","doi":"10.1016/j.gresc.2024.07.003","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.07.003","url":null,"abstract":"A highly selective and atom-economical multi-component remote difunctionalization strategy has been successfully developed. This strategy utilizes precise control over the radical properties of bifunctional precursors and the electronic traits of olefins and diazenes to achieve effective radical-mediated 1,4-oxyimination/diamination across C=C and N=N bonds. By capitalizing on compatibility and reactivity tuning, this approach enables the synthesis of complex triazine compounds with an framework, providing a versatile tool for constructing diverse molecular structures. This metal-free method is atom-efficient and adaptable to various substrates, demonstrating remarkable tolerance for a broad range of functional groups.","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"191 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142225513","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}
{"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}