Shuowen Wang , Rong Li , Shanping Chen , Guojiang Mao , Wen Shao , Guo-Jun Deng
{"title":"Chemoselective synthesis of α-carboline derivatives via hypervalent iodine-catalyzed [3+3] annulation under metal-free conditions","authors":"Shuowen Wang , Rong Li , Shanping Chen , Guojiang Mao , Wen Shao , Guo-Jun Deng","doi":"10.1016/j.gresc.2023.01.002","DOIUrl":"10.1016/j.gresc.2023.01.002","url":null,"abstract":"<div><p>A strategy for the synthesis of α-carboline derivatives from indole-3-carboxaldehydes and 3-aminocyclohex-2-enones under metal-free conditions has been developed. The combination use of phenyliodine (III) diacetate (PIDA) and benzoic acid could significantly facilitate the corresponding [3 + 3] annulation process. This newly developed strategy featured unextraordinary chemoselectivity, good functional group tolerance and the preservation of the carbonyl group of the ketone substrates, which offers the possibility for further transformation of the products.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 112-116"},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000029/pdfft?md5=397dc1e000f17da3a4d3b5908410689d&pid=1-s2.0-S2666554923000029-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80560629","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}
Yuting Chen , Guanghui Lv , Zhiyang Li , Meiling Ye , Tianle Huang , Li Hai , Yong Wu
{"title":"Rh(II) catalyzed efficient sigmatropic rearrangement reaction of pyridotriazoles and sulfides","authors":"Yuting Chen , Guanghui Lv , Zhiyang Li , Meiling Ye , Tianle Huang , Li Hai , Yong Wu","doi":"10.1016/j.gresc.2023.04.004","DOIUrl":"10.1016/j.gresc.2023.04.004","url":null,"abstract":"<div><p>The [2,3]- and [1,2]-sigmatropic rearrangement reactions between pyridotriazoles and sulfides catalyzed by rhodium(II) were investigated. The utilization of pyridotriazoles as the carbene precursors in this kind of reaction efficiently constructed the C(sp<sup>3</sup>)-S and C(sp<sup>3</sup>)-Se bond with broad substrate scope and great functional group tolerance.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 77-79"},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000339/pdfft?md5=d974594596fdf40dc9b7f441e906f029&pid=1-s2.0-S2666554923000339-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88627991","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":"Photochemical nitrene transfer reactions of iminoiodinanes with sulfoxides","authors":"Xuemei Zhao, Zhiyuan Tang, Linlin Shi, Yujing Guo, Rene M. Koenigs, Xinqi Hao","doi":"10.1016/j.gresc.2024.05.001","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.05.001","url":null,"abstract":"","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"24 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141049659","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}
Lingzhi Xie , Yun Zhang , Ruyue Zhang , Haibo Cui , Baodong Cui , Wenyong Han , Nanwei Wan , Zhi Li , Yongzheng Chen
{"title":"Biocatalytic stereoselective synthesis of methyl mandelates by engineering a cytochrome P450 hydroxylase","authors":"Lingzhi Xie , Yun Zhang , Ruyue Zhang , Haibo Cui , Baodong Cui , Wenyong Han , Nanwei Wan , Zhi Li , Yongzheng Chen","doi":"10.1016/j.gresc.2023.01.005","DOIUrl":"10.1016/j.gresc.2023.01.005","url":null,"abstract":"<div><p>Chiral methyl mandelates are useful synthons in organic transformation and pharmaceutical synthesis. Green synthesis of these valuable compounds by direct C–H activating oxidative hydroxylation has attracted keen interest. Described herein is achieving the stereoselective and efficient bio-hydroxylation of methyl 2-phenylacetates to the chiral methyl mandelates by directed evolution of the cytochrome P450DA hydroxylase. In the present study, a new colorimetric high-throughput screening assay was successfully developed based on a dual-enzyme cascade for the engineering of the P450DA's hydroxylation activity. Several beneficial variants with enhanced bio-hydroxylation activity were created by combining random mutagenesis and site-saturated/directed mutagenesis strategies. Whole-cell bio-hydroxylation of various methyl 2-phenylacetates using the best septuplet-mutant P450DA-11 yielded the corresponding chiral methyl mandelates in up to 92% isolated yields and >99% <em>ee</em>.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 88-93"},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000054/pdfft?md5=8b25d52d413e20f9e147427b5b961e35&pid=1-s2.0-S2666554923000054-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87468871","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}
Yongxing Li , Pengqian Luan , Lele Dong , Jianqiao Liu , Luying Jiang , Jing Bai , Fufeng Liu , Yanjun Jiang
{"title":"Asymmetric reduction of conjugated CC bonds by immobilized fusion of old yellow enzyme and glucose dehydrogenase","authors":"Yongxing Li , Pengqian Luan , Lele Dong , Jianqiao Liu , Luying Jiang , Jing Bai , Fufeng Liu , Yanjun Jiang","doi":"10.1016/j.gresc.2022.10.012","DOIUrl":"https://doi.org/10.1016/j.gresc.2022.10.012","url":null,"abstract":"<div><p>Asymmetric reduction of the conjugated C<img>C bonds by the old yellow enzymes (OYEs) presents a promising field in the synthesis of chiral chemicals. Nevertheless, few natural OYEs have been applied in large-scale applications due to the requirement of costly NADPH and low operational stability. Herein, a stable and efficient fusion of YqjM from <em>Bacillus subtilis</em> and glucose dehydrogenase (GDH) from <em>Bacillus megaterium</em> was constructed to stereoselectively reduce the conjugated C<img>C bonds in a self-sufficient continuous process. The effects of the enzyme order and different linkers on the fusions were investigated by structural analysis and all-atom molecular dynamics simulation. The best fusion YqjM_G_GDH gave 98% conversion of 100 mmol/L 2-methylcyclopentenone with an excellent <em>ee</em> value (>99%) in 3 h, while the mixture of individual enzymes only obtained 68% conversion after more than 8 h. The improved substrate conversion of YqjM_G_GDH fusion was probably attributed to the increased flexibility of each fused enzyme and the shortening of the diffusion distance of NADPH regenerated. A one-pot process was designed to purify and immobilize the fusion on the Ni<sup>2+</sup>-nitrilotriacetic acid functionalized magnetic mesoporous silica nanoflowers. The resulting immobilized biocatalyst not only catalyzed the asymmetric reduction of various <em>α,β</em>-unsaturated ketones (20 mmol/L) continuously with only 50 μmol/L NADP<sup>+</sup> to initiate the whole process, but also retained more than 82% of the initial activity after seven cycles, serving as a good candidate for the industrial applications.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 80-87"},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001119/pdfft?md5=e72d818078f5545af9df52bf008b7cf4&pid=1-s2.0-S2666554922001119-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141089938","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}
Matteo Formenti, M. Pagliaro, Cristina Della Pina, R. Ciriminna
{"title":"Graphene oxide in palladium nanoparticle (GrafeoPlad): a new class of functional materials","authors":"Matteo Formenti, M. Pagliaro, Cristina Della Pina, R. Ciriminna","doi":"10.1016/j.gresc.2024.04.004","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.04.004","url":null,"abstract":"","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"7 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141025324","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}
Yunting Liu , Na Guo , Weixi Kong , Shiqi Gao , Guanhua Liu , Liya Zhou , Jing Gao , Yanjun Jiang
{"title":"Magnetic wrinkled organosilica-based metal-enzyme integrated catalysts for enhanced chemoenzymatic catalysis","authors":"Yunting Liu , Na Guo , Weixi Kong , Shiqi Gao , Guanhua Liu , Liya Zhou , Jing Gao , Yanjun Jiang","doi":"10.1016/j.gresc.2023.01.008","DOIUrl":"10.1016/j.gresc.2023.01.008","url":null,"abstract":"<div><p>Core-shell structured magnetic wrinkled organosilica-based metal-enzyme integrated catalysts were synthesized, and their catalytic performances were studied in the chemoenzymatic dynamic kinetic resolution of chiral amines in an organic solvent, as well as in the chemoenzymatic synthesis of chiral alcohols in water. Structure-performance studies revealed the important influence of their tunable structure and composition on the optimization of activity, stability, and recyclability in chemoenzymatic catalysis.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 122-125"},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S266655492300008X/pdfft?md5=2f031f8db45b35bb91908c64863c0c0f&pid=1-s2.0-S266655492300008X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73950934","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}
Yike Bai, Wenhua Yu, Rong Chen, Guipeng Yu, Baosheng Wei
{"title":"Recent advances in transition-metal-free conversion of aldehydes to ketones","authors":"Yike Bai, Wenhua Yu, Rong Chen, Guipeng Yu, Baosheng Wei","doi":"10.1016/j.gresc.2024.04.007","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.04.007","url":null,"abstract":"","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"22 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141054150","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}