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Photoredox-catalyzed selective head-to-head reductive coupling of activated alkenes
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-25 DOI: 10.1039/d4qo02344g
Shenhao Chen, Zongchang Han, Han-Shi Hu, Jun Li, Chanjuan Xi
{"title":"Photoredox-catalyzed selective head-to-head reductive coupling of activated alkenes","authors":"Shenhao Chen, Zongchang Han, Han-Shi Hu, Jun Li, Chanjuan Xi","doi":"10.1039/d4qo02344g","DOIUrl":"https://doi.org/10.1039/d4qo02344g","url":null,"abstract":"Head-to-head reductive hydrodimerization of activated alkenes offers access to valuable bulk or fine chemicals, such as adipates or adiponitrile as an intermediate for industrial synthesis of nylon. We herein report a novel reaction to realize head-to-head reductive coupling of activated alkenes by a photoinduced Ir/PPh<small><sub>3</sub></small>/H<small><sub>2</sub></small>O system, providing mild access to various adipate derivatives in high chemo- and regioselectivity. In this reaction, a [Ph<small><sub>3</sub></small>P-OH] radical generated from a photoinduced interaction between H<small><sub>2</sub></small>O and PPh<small><sub>3</sub></small> enables the PCET process with activated alkenes to form C-centered radical at the β-position that is rarely reported.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"34 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Selective Functionalization of Trp residues via Copper-Catalyzed Ullmann Coupling
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02073a
Xinru Liang, Junjie Shi, Qiuju Zhong, Lai Li, Yutao Liu, Tong Sun, Junxi Liang, Xian-Ying Shi, Gao-Qiang Li, Mingyu Yang
{"title":"Selective Functionalization of Trp residues via Copper-Catalyzed Ullmann Coupling","authors":"Xinru Liang, Junjie Shi, Qiuju Zhong, Lai Li, Yutao Liu, Tong Sun, Junxi Liang, Xian-Ying Shi, Gao-Qiang Li, Mingyu Yang","doi":"10.1039/d4qo02073a","DOIUrl":"https://doi.org/10.1039/d4qo02073a","url":null,"abstract":"The modification of peptides can considerably change their functions, thus facilitating the development of peptides for use as drugs, therapeutics, diagnostics, and in chemical biology. Transition-metal catalyzed cross-coupling is a promising method to accomplish peptide modification, but the chemoselective introduction of a new C(sp2)−N bond at a tryptophan residue is a challenging yet crucial task. Herein, the functionalization of peptides achieved through the copper-catalyzed Ullmann coupling of tryptophan with aryl halides containing multiple functional groups is reported, which enabled the arylation of indole side chain of tryptophan. This method is featured with remarkable tolerance of diverse functional groups, scalability, and distinct chemoselectivity toward tryptophan residues. The fusion of different functional groups demonstrated the potential utility of this approach, offering new avenues to modify the side chains of proteinogenic amino acids.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027042","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Modular supramolecular capsules based on α,γ-cyclic peptide dimers for the development of confined catalysis
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02270j
Ezequiel Troncoso Mondragón, Alberto Fuertes, Martín Calvelo, Angel L. Fuentes de Arriba, Manuel Amorín, Juan R Granja
{"title":"Modular supramolecular capsules based on α,γ-cyclic peptide dimers for the development of confined catalysis","authors":"Ezequiel Troncoso Mondragón, Alberto Fuertes, Martín Calvelo, Angel L. Fuentes de Arriba, Manuel Amorín, Juan R Granja","doi":"10.1039/d4qo02270j","DOIUrl":"https://doi.org/10.1039/d4qo02270j","url":null,"abstract":"A modular strategy is designed for the preparation of supramolecular capsules in the search for new functional containers. The strategy is based on the use of the self-assembly properties of α,γ-cyclic octapeptide to form toroidal dimers in which two reactive points are incorporated to anchor molecular caps in the last stage of the synthesis. In this way, the used caps, which are decorated with catalytic metal complex, are easily intechangeable allowing searching for new catalytic properties.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Visible-light-mediated C−S bond activation in cysteine derivatives with quinoxalinones for the synthesis of heteroaryl amino acids
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02213k
Xinyao Li, Shuqi Ling, Jingjie Hai
{"title":"Visible-light-mediated C−S bond activation in cysteine derivatives with quinoxalinones for the synthesis of heteroaryl amino acids","authors":"Xinyao Li, Shuqi Ling, Jingjie Hai","doi":"10.1039/d4qo02213k","DOIUrl":"https://doi.org/10.1039/d4qo02213k","url":null,"abstract":"The synthetic strategies for selective chemical modification of natural amino acids and peptides are constantly in great needs in current state-of-the-art therapeutics. Herein, we report a photocatalytic C−S bond activation in cysteine derivatives with quinoxalinones for the synthesis of pharmacologically interesting heteroaryl amino acids. A series of quinoxalinone-conjugated amino acids and oligopeptides as well as caffeine- and isoquinoline-contained amino acids were efficiently obtained through desulfurative heteroarylation of cysteine derivatives. The given approach features with wide substrate scope, mild conditions, good yields and operational simplicity. Furthermore, the N-propargyl quinoxalinone-conjugated amino acids produced can be successfully integrated with biotin-PEG3-azide through Click chemistry for potential applications in immunology and histochemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027043","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Total synthesis of cyclopropane-containing natural products: recent progress (2016–2024)
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02316a
Neng Wang, Jin-Xin Zhao, Jian-Min Yue
{"title":"Total synthesis of cyclopropane-containing natural products: recent progress (2016–2024)","authors":"Neng Wang, Jin-Xin Zhao, Jian-Min Yue","doi":"10.1039/d4qo02316a","DOIUrl":"https://doi.org/10.1039/d4qo02316a","url":null,"abstract":"Cyclopropane, as the smallest all-carbon ring, is a ubiquitous functional group found in many complex natural products, such as terpenoids, alkaloids, steroids, and fatty acids. Natural products containing cyclopropane motifs have attracted burgeoning interests owing to their fascinating architectural features and versatile biological properties. In recent decades, a variety of methods for the construction of cyclopropane rings have emerged, which can be mainly classified into [2 + 1]-type cycloaddition and direct 1,3-cyclization. These methods have been extensively utilized by synthetic chemists in their pursuit of synthesizing cyclopropane-containing natural products. This review outlines recent progress in this research area, with a particular focus on the ingenious application of novel synthetic methodologies and tactics for assembling naturally occurring three-membered rings, aiming to complement existing literature in this field.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"87 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027050","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
An Access to Chiral 3-Benzylchromanones and 2,6-Disubstituted Cyclohexanones via Rh-Catalyzed Chemo- and Enantioselective Hydrogenation of Arylidene Chromanones/Cyclohexanones†
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02376e
Qianling Guo, Chaochao Xie, Guofu Zi, Yuping Huang, Guohua Hou
{"title":"An Access to Chiral 3-Benzylchromanones and 2,6-Disubstituted Cyclohexanones via Rh-Catalyzed Chemo- and Enantioselective Hydrogenation of Arylidene Chromanones/Cyclohexanones†","authors":"Qianling Guo, Chaochao Xie, Guofu Zi, Yuping Huang, Guohua Hou","doi":"10.1039/d4qo02376e","DOIUrl":"https://doi.org/10.1039/d4qo02376e","url":null,"abstract":"A highly chemo- and enantioselective hydrogenation of arylidene chromanones/cyclohexanones catalyzed by the Rh-f-spiroPhos complex has been developed, providing a series of chiral 3-benzylchromanones in high yields (93−99%) with excellent enantioselectivities (up to 98% ee) and achieving high turnover numbers (TON = 2000). Furthermore, an efficient desymmetrizing enantioselective hydrogenation of 3,5-dibenzylidene chromanones and 2,6-dibenzylidene cyclohexanones has also been realized, delivering chiral dibenzyl chromanones/cyclohexanones with excellent chemo-, diastereo- and enantioselectivities (up to &gt;20:1 dr, &gt;99% ee). This methodology provides a straightforward and mild access to asymmetric synthesis of α-chiral ketones.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Ligand-Enabled Enantio- and Site-selective Remote C-H Arylation of 2-(2-Phenpropyl)pyridine Derivatives
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-24 DOI: 10.1039/d4qo02236j
Li Hong-Liang, Dai-Yu Li, Jing-Ping Li, Shunsuke Yabu, Lisheng Wang, Hirofumi Sato, Masahiro Higashi, Yoichiro Kuninobu
{"title":"Ligand-Enabled Enantio- and Site-selective Remote C-H Arylation of 2-(2-Phenpropyl)pyridine Derivatives","authors":"Li Hong-Liang, Dai-Yu Li, Jing-Ping Li, Shunsuke Yabu, Lisheng Wang, Hirofumi Sato, Masahiro Higashi, Yoichiro Kuninobu","doi":"10.1039/d4qo02236j","DOIUrl":"https://doi.org/10.1039/d4qo02236j","url":null,"abstract":"The great potential of transition metal-catalyzed C–H functionalization is precisely selective reactions at the specific C–H bonds in complex molecules. Therefore, the development of enantio- and site-selective C–H functionalization is a long-term pursuit in this field. Herein, we disclose a ligand-enabled enantio- and site-selective remote C–H arylation of 2-(2-phenylpropyl)pyridine derivatives. The combination of an acetyl-protected aminoethyl phenyl thioether (MPA-thiol) with aryl iodides is found to enable -C(sp3)–H arylation, whereas L-pyroglutamic acid (L-pGlu) promotes the -C(sp2)–H cross-coupling with various Aryl-Bpin. Notably, both C–H arylations proceed with high enantioselectivity and good yields. The results of DFT calculation support the enantioselectivity and site-selectivity of these two C–H arylations. Moreover, the utilities of this transformation were demonstrated by derivatization of harmane alkaloid, gram-scale reaction and the successful removal of the pyridyl directing group.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"61 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Combination of the structural components of amino acids with fatty acids: Access to an unknown class of “fatty” -amino acids by palladium-catalyzed amidocarbonylation 氨基酸与脂肪酸结构组分的结合：通过钯催化氨基羰基化获得未知类别的“脂肪”-氨基酸
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-23 DOI: 10.1039/d4qo01127a
Mohammed Asadpour, Edson Leonardo Scarpa de Souza, Matthias Beller, Anke Spannenberg, Helfried Neumann, Carlos Roque Correia
{"title":"Combination of the structural components of amino acids with fatty acids: Access to an unknown class of “fatty” -amino acids by palladium-catalyzed amidocarbonylation","authors":"Mohammed Asadpour, Edson Leonardo Scarpa de Souza, Matthias Beller, Anke Spannenberg, Helfried Neumann, Carlos Roque Correia","doi":"10.1039/d4qo01127a","DOIUrl":"https://doi.org/10.1039/d4qo01127a","url":null,"abstract":"A new class of amino acids, so-called fatty amino acids, which integrate the typical structural motif of another important type of natural products, fatty acids, is presented. Applying the palladium-catalyzed amidocarbonylation, diverse new N-acyl fatty amino acids are synthesized in one step in 100% atom-efficient manner. Utilizing small amounts (0.5 mol%) of simple commercial Pd(OAc)2 the desired products can be synthesized in good to high yields in up to multi-g-scale. The shown products represent a combination of two essential classes of natural products and provides new bio-based building blocks with potential for many applications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143020529","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Copper-catalyzed Büchner reaction and phenyl cyclopropanation through diyne cyclization 铜催化的<s:1> chner反应及苯基环丙烷的双炔环化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-22 DOI: 10.1039/d4qo02371d
Tong Li, Jia-Juan He, Kai-Yu Fan, Long-Wu Ye, Bo Zhou, Xin-Qi Zhu
{"title":"Copper-catalyzed Büchner reaction and phenyl cyclopropanation through diyne cyclization","authors":"Tong Li, Jia-Juan He, Kai-Yu Fan, Long-Wu Ye, Bo Zhou, Xin-Qi Zhu","doi":"10.1039/d4qo02371d","DOIUrl":"https://doi.org/10.1039/d4qo02371d","url":null,"abstract":"Büchner reaction, as an exclusive category of expansive dearomatization, represents a powerful approach for the construction of valuable functionalized cycloheptatrienes in a direct manner from readily available aromatic precursors. However, the traditional Büchner reaction almost relies on using explosive diazo compounds as the carbene precursors. Herein, we disclose a copper-catalyzed Büchner reaction through diyne cyclization, and bicycle-fused cycloheptatrienes bearing all carbon quaternary stereogenic centers are obtained in moderate to excellent yields with broad substrate scope. In addition, norcaradiene derivatives can also be selectively produced by a substrate control through a phenyl cyclopropanation reaction, thus constituting a copper-catalyzed controllable cyclization of diynes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"49 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142991925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Iron(III)-catalyzed mono-, di- and tricyanomethylation of primary amines with diazoacetonitrile: Construction of α-amino acetonitriles and asymmetric α-amino succinonitriles 铁（III）催化伯胺与重氮乙腈的一甲基化、二甲基化和三甲基化：α-氨基乙腈和不对称α-氨基丁二腈的构建
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-01-22 DOI: 10.1039/d4qo02218a
Gang Wang, Yu-Heng Zeng, Qian-Yu Jiang, Jia-Yi Chen, Rong Zhou, Huai-Bo Zou
{"title":"Iron(III)-catalyzed mono-, di- and tricyanomethylation of primary amines with diazoacetonitrile: Construction of α-amino acetonitriles and asymmetric α-amino succinonitriles","authors":"Gang Wang, Yu-Heng Zeng, Qian-Yu Jiang, Jia-Yi Chen, Rong Zhou, Huai-Bo Zou","doi":"10.1039/d4qo02218a","DOIUrl":"https://doi.org/10.1039/d4qo02218a","url":null,"abstract":"α-Amino nitriles and succinonitriles are two important classes of cyano-containing compounds with extremely significant application value. Herein, we firstly reported the divergent synthesis for preparing α-amino nitriles and asymmetric α-amino succinonitriles via the developed mono-, di- and tricyanomethylation between primary amines with diazoacetonitrile catalyzed by (TPP)Fe(III)Cl or PcFe(III)Cl in sole dichloromethane (DCM) or the mixed solvent of DCM and acetonitrile at room temperature. Within the divergent synthesis, the combination of the mono- and dicyanomethylation is a new example around solvent control divergent synthesis; both of the di- and tricyanomethylation represent a novel type of transformation in the field of metalloradical catalysis, which can construct one C−C bond &amp; two or three C−N bonds in one-pot and are totally different from the conventional N−H insertion between amines with diazo reagents; additionally, the divergent synthesis can be used for the gram-scale preparation of three typical compounds. For the proposed mechanism, the monocyanomethylation proceeds by the N−H insertion pathway; while for the di- and tricyanomethylation, the homodimerization of iron(III)−acetonitrile radical derived from the reaction between diazoacetonitrile and (TPP)Fe(III)Cl coordinated by bis(amines) or PcFe(III)Cl is involved, and the attack of one amine molecule toward one carbon on the formed C−C bond (monoamination) is followed.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142992609","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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