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Facile synthesis and anion binding properties of a preorganized macrocyclic receptor.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-02 DOI: 10.1039/d4ob01760a
Channi Cheng, Zhengxiang Li, Dezhi Zhao, Chengyou Han
{"title":"Facile synthesis and anion binding properties of a preorganized macrocyclic receptor.","authors":"Channi Cheng, Zhengxiang Li, Dezhi Zhao, Chengyou Han","doi":"10.1039/d4ob01760a","DOIUrl":"https://doi.org/10.1039/d4ob01760a","url":null,"abstract":"<p><p>Herein, we report a novel Schiff base macrocyclic receptor (MR). The structure of MR was characterized by NMR, UV-vis and fluorescence spectroscopy, revealing that it was a rigid and preorganized planar π-conjugated fluorescent macrocycle. Furthermore, MR showed effective binding properties with tetrabutylammonium halides TBAX (X = Cl, Br, and I) which were investigated by the NMR titration method and molecular modelling.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764746","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Cross-bridged cyclam derivatives with bis(phosphinate) and phosphinate-phosphonate pendant arms (cb-BPC) as chelators for copper radioisotopes.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-29 DOI: 10.1039/d4ob01473a
Peter Urbanovský, Tomáš David, Veronika Hlinová, Vojtěch Kubíček, Hans-Jürgen Pietzsch, Petr Hermann
{"title":"Cross-bridged cyclam derivatives with bis(phosphinate) and phosphinate-phosphonate pendant arms (cb-BPC) as chelators for copper radioisotopes.","authors":"Peter Urbanovský, Tomáš David, Veronika Hlinová, Vojtěch Kubíček, Hans-Jürgen Pietzsch, Petr Hermann","doi":"10.1039/d4ob01473a","DOIUrl":"https://doi.org/10.1039/d4ob01473a","url":null,"abstract":"<p><p>Copper radioisotopes can be used for imaging as well as for therapy and, thus, can form ideal theranostic pairs. The Cu(II) complexes of cross-bridged cyclam (cb-cyclam) derivatives are considered to be highly stable <i>in vivo</i>. However, the complexes are mostly formed under harsh conditions not compatible with sensitive biomolecules. Here, a new class of cb-cyclam derivatives, cross-bridged bis(phosphinate)cyclams (\"cb-BPC\"), were investigated. Ligands with one or two methylene-bis(phosphinate) -CH<sub>2</sub>-PO<sub>2</sub>H-CH<sub>2</sub>-PO<sub>2</sub>H(R) (R = H, OH, substituted alkyl) pendant arms were synthesized. Bifunctionalization on the distant phosphorus atom was carried out by employing <i>P</i>-nitrobenzyl (R = CH<sub>2</sub>-Ph-4-NO<sub>2</sub>) precursors and/or, for cb-BPC with two bis(phosphinate) pendant arms, by reactions of silyl-phosphites obtained by silylation of their P(O)-H fragments. The reactive bifunctional groups include amine, carboxylate, azide, isothiocyanate, maleimide and/or tetrazine, and also their orthogonally reactive combination in a single molecule of chelator. The cb-BPCs with one bis(phosphinate) arm were not efficiently radiolabelled with <sup>64</sup>Cu. The cb-BPCs with two pendant arms were radiolabelled even at room temperature and with only a small excess of chelator, leading to a high specific activity. Radiolabelling was fully comparable with that of analogous bis(phosphinate) derivatives of cyclam and identical radiolabelling of cyclam and cb-cyclam derivatives was observed for the first time. The cb-BPCs with two bis(phosphinate) pendant arms represent a new class of rigid chelators for copper radioisotopes that are easily synthetically modifiable, highly hydrophilic and radiolabelled under mild conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142749427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Synthesis of alkyl sulfones via a photocatalytic multicomponent reaction of aryldiazo tetrafluoroborate salts, styrene derivatives, and sodium metabisulfite.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-29 DOI: 10.1039/d4ob01664e
Truong Giang Luu, Hee-Kwon Kim
{"title":"Synthesis of alkyl sulfones <i>via</i> a photocatalytic multicomponent reaction of aryldiazo tetrafluoroborate salts, styrene derivatives, and sodium metabisulfite.","authors":"Truong Giang Luu, Hee-Kwon Kim","doi":"10.1039/d4ob01664e","DOIUrl":"https://doi.org/10.1039/d4ob01664e","url":null,"abstract":"<p><p>Alkyl sulfones are found in numerous valuable organic molecules. Here, we describe a promising approach for the one-pot synthesis of alkyl sulfones under visible light. Aryl diazo salts were allowed to react with styrene derivatives and sodium metabisulfite in the presence of thiophenol as a hydrogen atom transfer reagent and rhodamine B as a photocatalyst to yield alkyl sulfones. Using this process, various alkyl sulfones were readily synthesized under mild reaction conditions. Our results suggest that this approach can provide diverse and valuable sulfones.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142749428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Forging the tricyclic core framework of euphordraculoate B via a Barbier-type allyl addition. 通过巴比耶型烯丙基加成法锻造 euphordraculoate B 的三环核心框架。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-28 DOI: 10.1039/d4ob01743a
Lingduan Meng, Jingjing Liu, Zeying Sun, Yangdong Hou, Qingyun Huang, Pingping Tang
{"title":"Forging the tricyclic core framework of euphordraculoate B <i>via</i> a Barbier-type allyl addition.","authors":"Lingduan Meng, Jingjing Liu, Zeying Sun, Yangdong Hou, Qingyun Huang, Pingping Tang","doi":"10.1039/d4ob01743a","DOIUrl":"https://doi.org/10.1039/d4ob01743a","url":null,"abstract":"<p><p>A novel strategy for the synthesis of an advanced intermediate <i>en route</i> to the tigliane derivative euphordraculoate B was described, which led to the successful construction of the 5/5/6 tricyclic core framework as well as the multiple consecutive stereocenters on the skeleton. Key steps of the strategy include a chlorination reaction, an aldol reaction, and a Barbier-type allyl addition.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737835","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Mild defluorinative N-acrylation of amines with (trifluoromethyl)alkenes: synthesis of α-arylacrylamides. 胺与（三氟甲基）烯的温和脱氟 N-丙烯化反应：α-芳基丙烯酰胺的合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-28 DOI: 10.1039/d4ob01554a
Yuqi Li, Rongbin Peng, Zhaolong Ma, Zhihui Wang, Chuanle Zhu
{"title":"Mild defluorinative <i>N</i>-acrylation of amines with (trifluoromethyl)alkenes: synthesis of α-arylacrylamides.","authors":"Yuqi Li, Rongbin Peng, Zhaolong Ma, Zhihui Wang, Chuanle Zhu","doi":"10.1039/d4ob01554a","DOIUrl":"https://doi.org/10.1039/d4ob01554a","url":null,"abstract":"<p><p>A practical and efficient method for the <i>N</i>-acrylation of amines with (trifluoromethyl)alkenes is achieved <i>via</i> the cleavage of three C(sp<sup>3</sup>)-F bonds, affording a diverse range of useful tertiary and secondary α-arylacrylamides in high yields. This protocol features mild conditions, is transition-metal free, operationally simple, gram-scalable, and compatible with valuable functional groups, and has a broad substrate scope. Mechanistic studies indicate that exchange of an oxygen atom happens between H<sub>2</sub>O and NaOH, and that the oxygen atom is incorporated into the α-arylacrylamides <i>via</i> the <i>ipso</i>-defluorooxylation of the (trifluoromethyl)alkene. This method is also applied in the late-stage <i>N</i>-acrylation of pharmaceuticals.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737838","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
One-pot hydroaminomethylation of an alkene under formation of primary amines by combining hydroformylation at elevated syngas pressure and biocatalytic transamination in water. 通过在合成气高压下进行加氢甲酰化反应和在水中进行生物催化转氨作用，在伯胺形成的条件下对烯烃进行一次性加氢氨基甲基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-28 DOI: 10.1039/d4ob01513d
Jonas Spang, Hannah Bork, Feodor Belov, Jan von Langermann, Andreas J Vorholt, Harald Gröger
{"title":"One-pot hydroaminomethylation of an alkene under formation of primary amines by combining hydroformylation at elevated syngas pressure and biocatalytic transamination in water.","authors":"Jonas Spang, Hannah Bork, Feodor Belov, Jan von Langermann, Andreas J Vorholt, Harald Gröger","doi":"10.1039/d4ob01513d","DOIUrl":"https://doi.org/10.1039/d4ob01513d","url":null,"abstract":"<p><p>We report a novel one-pot chemoenzymatic synthesis of primary amines in water, combining rhodium-catalysed hydroformylation of styrene with a biocatalytic transamination. This process is starting from styrene at 50 mM substrate loading on a 10 mL preparative scale. Combined towards a one-pot process with both steps running concurrently, this chemoenzymatic synthesis involves a 6-DPPon/rhodium-catalysed hydroformylation of styrene at 20 bar of syngas, forming the <i>iso</i>- and <i>n</i>-aldehydes and an enzymatic transamination of the <i>in situ</i>-formed aldehydes to the corresponding primary amines catalysed by the amine transaminase from <i>Chromobacterium violaceum</i>, yielding the desired primary amines with 99% conversion.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737848","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Rhodium(III)-catalyzed direct C-H activation of 2-aryl-3H-indoles: a strategy for 4-heteroaryl pyrazole synthesis. 铑（III）催化的 2-芳基-3H-吲哚的直接 C-H 活化：4-庚芳基吡唑的合成策略。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01655f
Zi Yang, Ji Luo, Wenbo Zhang, Jieni Lei, Chaoshui Liu, Yaqian Li
{"title":"Rhodium(III)-catalyzed direct C-H activation of 2-aryl-3<i>H</i>-indoles: a strategy for 4-heteroaryl pyrazole synthesis.","authors":"Zi Yang, Ji Luo, Wenbo Zhang, Jieni Lei, Chaoshui Liu, Yaqian Li","doi":"10.1039/d4ob01655f","DOIUrl":"https://doi.org/10.1039/d4ob01655f","url":null,"abstract":"<p><p>A novel protocol for synthesizing 4-heteroaryl pyrazoles from readily available 2-aryl-3<i>H</i>-indoles and diazopyrazolones through the rhodium(III)-catalyzed C-H bond activation has been achieved. This redox-neutral strategy features powerful reactivity, tolerates various functional groups, and proceeds with moderate yields under mild reaction conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724311","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Coordination complexes of PIII-doped heterobuckybowls and their applications in catalysis. 掺杂 PIII 的异巴基络合物及其在催化中的应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01737d
Lijun Feng, Xinqiang Hua, Jihai Shang, Xiangfeng Shao
{"title":"Coordination complexes of P<sup>III</sup>-doped heterobuckybowls and their applications in catalysis.","authors":"Lijun Feng, Xinqiang Hua, Jihai Shang, Xiangfeng Shao","doi":"10.1039/d4ob01737d","DOIUrl":"https://doi.org/10.1039/d4ob01737d","url":null,"abstract":"<p><p>Doping the π-frameworks of polycyclic aromatic hydrocarbons (PAHs) with main-group elements is a powerful strategy to manipulate optoelectronic properties. Herein, the benzylic carbons of π-bowl sumanene are replaced with chalcogens (S, Se, and Te) and trivalent phosphorus (P<sup>III</sup>), affording a series of P<sup>III</sup>-doped heterosumanenes (HSEs). The lone-pair electrons of the P<sup>III</sup>-dopant endow these HSEs with pronounced affinity toward transition metals (Au<sup>+</sup>, Pt<sup>2+</sup>, and Pd<sup>2+</sup>). Accordingly, nine coordination complexes were synthesized to exhibit diverse coordination patterns contingent upon the metal ions and chalcogen atoms on HSEs. For the first time, we proved that the Pd<sup>2+</sup> complexes of these HSEs are promising catalysts for the Suzuki-Miyaura coupling reaction of aryl chlorides.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Iridium-catalyzed tandem olefination/aza-Michael reaction: rapid access to N-N functionalized hydrazides. 铱催化的串联烯化/aza-迈克尔反应：快速获得 N-N 官能化肼。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01631a
Chao Zhang, Lin Dong
{"title":"Iridium-catalyzed tandem olefination/aza-Michael reaction: rapid access to N-N functionalized hydrazides.","authors":"Chao Zhang, Lin Dong","doi":"10.1039/d4ob01631a","DOIUrl":"https://doi.org/10.1039/d4ob01631a","url":null,"abstract":"<p><p>An Ir-catalyzed tandem olefination/aza-Michael reaction of protected benzoylhydrazine derivatives with olefins under mild conditions has been developed. This method can be successfully applied to the construction of various structurally N-N-functionalized hydrazide derivatives bearing the α,β-unsaturated side chain in good to excellent yields. In particular, the deaminoprotected products can be used as potential precursors for the construction of N-N axially chiral compounds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724309","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Chiral iodine-catalyzed asymmetric oxyamination of unactivated olefins. 手性碘催化未活化烯烃的不对称氧合反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01575d
Gui-Ping Han, Jia-Qi Wang, Jing-Feng Zhao, Dao-Yong Zhu, Lu-Wen Zhang, Wei He
{"title":"Chiral iodine-catalyzed asymmetric oxyamination of unactivated olefins.","authors":"Gui-Ping Han, Jia-Qi Wang, Jing-Feng Zhao, Dao-Yong Zhu, Lu-Wen Zhang, Wei He","doi":"10.1039/d4ob01575d","DOIUrl":"https://doi.org/10.1039/d4ob01575d","url":null,"abstract":"<p><p>In this paper, chiral aryl iodides were used for the first time to catalyze the formation of C-O and C-N bonds of inactive olefins to obtain optically active aminolactone derivatives. The reaction is compatible with various substituted alkenyl carboxylic acid substrates. This method usually shows high activity and enantioselectivity, with a yield of up to 83% and an ee of up to 99%. It is recovery and reuse of chiral aryl iodide catalyst CIC4 showed almost no loss in product yield and enantioselectivity after 3 runs.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
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