Organic Chemistry Frontiers最新文献_第7页

Divergent synthesis of two polycyclic frameworks containing tricyclic bridgehead carbon centers by gold-catalyzed cycloisomerization of o-cyclopropylidenemethyl-o′-alkynylbiaryls 金催化邻环丙基甲基-o′-炔基二芳基环异构化合成含三环桥头堡碳中心的两个多环框架

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-26 DOI: 10.1039/d5qo00816f

Lucía Sánchez-Jiménez, Adrián Gargantiel, Manuel A. Fernández-Rodríguez, Patricia García-García

引用次数: 0

Pd-Catalyzed Hydroesterification of Vinyl Cyclopropanes with Aryl Formates pd催化乙烯基环丙烷与甲酸芳酯的加氢酯化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-26 DOI: 10.1039/d5qo00634a

Junhua Li, Chunyin Li, Jing Li, Zhanwei Wang, Fengyin Wang, Yian Shi

引用次数: 0

Light-Promoted Cobalt-Catalyzed Radical Markovnikov Hydrothiolation of Alkenes with N-Arylsulfenyl Phthalimides 光促进钴催化烯烃与n -芳基亚砜基邻苯二胺的自由基Markovnikov氢硫化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-22 DOI: 10.1039/d5qo01020a

Xiang-Rui Li, Rong-Jin Zhang, Ting-Ting Miao, Yonghong Xiao, Kun-Quan Chen, Jian-Ji Zhong

{"title":"Light-Promoted Cobalt-Catalyzed Radical Markovnikov Hydrothiolation of Alkenes with N-Arylsulfenyl Phthalimides","authors":"Xiang-Rui Li, Rong-Jin Zhang, Ting-Ting Miao, Yonghong Xiao, Kun-Quan Chen, Jian-Ji Zhong","doi":"10.1039/d5qo01020a","DOIUrl":"https://doi.org/10.1039/d5qo01020a","url":null,"abstract":"In recent years, transition-metal hydride catalysis has emerged as a powerful strategy for radical Markovnikov hydrothiolation of alkenes, providing efficient access to branched thioethers. However, this approach remains underexplored, with existing methods often hampered by limitations such as the reliance on silane reductants, the need for specialized sulfide nucleophiles or radical acceptors, or the use of external oxidants. Herein, we report a new light-promoted cobalt-catalyzed system that employs Hantzsch ester as a mild hydride source for the radical Markovnikov hydrothiolation of alkenes using N-arylsulfenyl phthalimides as thiyl radical precursors. Notably, when allylic arenes were employed as substrates, a metal-hydride hydrogen atom transfer (MHAT)/retro-MHAT process occurred, enabling the synthesis of branched benzyl sulfides, which was unattainable under conventional catalytic conditions. Mechanistic investigations support the proposed reaction pathway. This method exhibits excellent regioselectivity, broad functional group compatibility, and applicability in late-stage functionalization.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144898832","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

Diastereo- and enantioselective construction of 1,4-nonadjacent alkyne-tethered products through CuI-promoted deprotonation and addition of terminal alkynes 通过cui促进的去质子化和末端炔的加成，非相邻1,4炔系链产物的非立体和对映选择性构建

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-22 DOI: 10.1039/d5qo00995b

Jiale Zheng, Wan-Hong Yuan, Han-Wen Zheng, Wei Du, Ying-Chun Chen

{"title":"Diastereo- and enantioselective construction of 1,4-nonadjacent alkyne-tethered products through CuI-promoted deprotonation and addition of terminal alkynes","authors":"Jiale Zheng, Wan-Hong Yuan, Han-Wen Zheng, Wei Du, Ying-Chun Chen","doi":"10.1039/d5qo00995b","DOIUrl":"https://doi.org/10.1039/d5qo00995b","url":null,"abstract":"While catalytic asymmetric alkynylation reaction has been extensively studied, existing examples predominantly focus on the construction of stereogenic center at the addition site. Here we disclose a chiral CuI complex-catalysed asymmetric alkynylation reaction of prochiral terminal diynes, which can furnish a diversity of products with challenging remote alkyne-tethered 1,4-central chirality. Mechanistic studies demonstrate that the initial desymmetrisative deprotonation of terminal diynes mediated by a chiral π-acidic CuI complex plays a crucial role in governing the diastereoselectivity, while the nucleophilic alkynylation step determines the enantiocontrol in whole process. This strategy can be extended to kinetic transformation of racemic terminal alkynes successfully. Such a stepwise asymmetric deprotonation and alkynylation strategy facilitated by a single chiral catalyst provides a robust platform for diastereo- and enantioselective construction of products having challenging rectilinear 1,4-central chirality.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"95 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144898833","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

Cooperative N-heterocyclic carbene/photocatalysis: visible-light-promoted tandem α-sp3 C–H activation and reductive N-alkylation of tetrahydroisoquinoline n -杂环碳/光协同催化：可见光促进四氢异喹啉串联α-sp3 C-H活化和n -还原烷基化

IF 4.7 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-19 DOI: 10.1039/D5QO01032B

Karthiyayini Gnanaoli, Deepan Babu Rajkumar and C. Uma Maheswari

{"title":"Cooperative N-heterocyclic carbene/photocatalysis: visible-light-promoted tandem α-sp3 C–H activation and reductive N-alkylation of tetrahydroisoquinoline","authors":"Karthiyayini Gnanaoli, Deepan Babu Rajkumar and C. Uma Maheswari","doi":"10.1039/D5QO01032B","DOIUrl":"https://doi.org/10.1039/D5QO01032B","url":null,"abstract":"While N-heterocyclic carbenes (NHCs) play a vital role as organocatalysts due to their umpolung reactivity toward carbonyl or imine carbons, activation of sp3-carbons via single-electron transfer (SET) processes remains challenging and underdeveloped. Recently, the coupling of NHC catalysis with photocatalysis for the SET process has gained attention. Herein, we report visible-light and NHC-catalyzed tandem α-sp3 C–H activation and reductive N-alkylation of tetrahydroisoquinoline (THIQ) with o-hydroxybenzaldehydes. The key step in this process is the formation of a photoactive species between o-hydroxybenzaldehydes and a base, which functions as a self-photocatalyst, eliminating the need for an external photocatalyst or photoactivator. The subsequent reaction of photoactive species with NHCs leads to the Breslow intermediate, followed by intramolecular hydrogen atom transfer (HAT) and benzylic activation to form N-benzylated 3,4-dihydroisoquinolin-1(2H)-ones. The salient features of this work include the use of sunlight as a visible-light source and molecular oxygen as an oxidant under mild reaction conditions, highlighting the green chemistry aspects of this approach.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 19","pages":" 5136-5145"},"PeriodicalIF":4.7,"publicationDate":"2025-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145110381","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

Nickel-catalyzed [4 + 1] sila-cycloaddition: a divergent synthesis of silacarbocycles from trichlorosilanes 镍催化的[4 + 1]硅环加成：三氯硅烷发散合成硅碳环

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-18 DOI: 10.1039/d5qo01018g

Liangliang Qi, Peng-Fei Xu, Yu-Ke Wu, Xiaobo Pang, Xing-Zhong Shu

引用次数: 0

Manipulating stereo-communication in binaphthol-bridged - and -cyclodextrins to develop -selective chiroptical pH switching and anion sensing in water 操纵联萘酚桥接-和-环糊精中的立体通信，以开发水中-选择性的热带pH开关和阴离子传感

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-16 DOI: 10.1039/d5qo00910c

Giovanni Preda, Sonia La Cognata, Laura Pedraza, Laurine Carlier, Maxime Kolb, Gennaro Pescitelli, Valeria Amendola, Dominique Armspach, Dario Pasini

{"title":"Manipulating stereo-communication in binaphthol-bridged - and -cyclodextrins to develop -selective chiroptical pH switching and anion sensing in water","authors":"Giovanni Preda, Sonia La Cognata, Laura Pedraza, Laurine Carlier, Maxime Kolb, Gennaro Pescitelli, Valeria Amendola, Dominique Armspach, Dario Pasini","doi":"10.1039/d5qo00910c","DOIUrl":"https://doi.org/10.1039/d5qo00910c","url":null,"abstract":"Molecular structures comprising naturally-occurring, stereodefined cyclodextrins and binaphthyls as bridging units have been realized, designed in such a way that the stereocommunication mode between the two chiral entities is unfavourable ('chiral mismatch'). The induced strain translates into highly responsive chiroptical behavior. On one side, the binaphthol-containing structure functions as a pH-controlled, single-molecule chiroptical switch, with reversal of the optical activity from acidic to basic conditions in a fully reversible manner. Additionally, the same host molecule demonstrates a pronounced chiroptical response to perrhenate in aqueous solution at pH 2.5, showing excellent selectivity for this specific anion. Computational analysis confirmed that the major effect of ReO4– complexation is making new conformations accessible to the binaphthol moiety with a large variation of the associated dihedral angles.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"70 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144857933","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

Rhodium-Catalyzed Hydroselenation of Unsymmetric 1,3-Dienes with 3,4-Markovnikov Regioselectivity 铑催化具有3,4- markovnikov区选择性的不对称1,3-二烯的加氢硒化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-14 DOI: 10.1039/d5qo00926j

Anee Taj, Chen Cui, Zhenwei Shi, Xuebin Huang, Xiao-Hui Yang

引用次数: 0

Photocatalytic Ketone Synthesis: Recent Advances in Radical-Based Approaches from Carboxylic Acids and Derivatives 光催化酮合成：羧酸及其衍生物自由基基合成方法的最新进展

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-08-14 DOI: 10.1039/d5qo01059d

Xiaochen Wang, Shengbiao Yang, Lan Bao, Tianzhen Wang, Lingang Wu, Qingmin Wang

引用次数: 0

Palladium/photoredox-catalysis in decarboxylative radical C(sp3)-C(sp3) cross-coupling reaction of γ-methylidene-δ-valerolactones with alkyl carboxylic acids 钯/光氧化催化γ-甲基-δ-戊内酯与烷基羧酸脱羧自由基C(sp3)-C（sp3）交叉偶联反应