Organic & Biomolecular Chemistry最新文献_第3页

Recent advancements in the Ullmann homocoupling reaction for the synthesis of biaryl compounds.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-03 DOI: 10.1039/d5ob00392j

Saima Perveen, Guoxiang Zhang, Pengfei Li

{"title":"Recent advancements in the Ullmann homocoupling reaction for the synthesis of biaryl compounds.","authors":"Saima Perveen, Guoxiang Zhang, Pengfei Li","doi":"10.1039/d5ob00392j","DOIUrl":"https://doi.org/10.1039/d5ob00392j","url":null,"abstract":"In the realm of biaryl synthesis, the Ullmann homocoupling reaction is a fundamental process for constructing biaryl compounds and has historically been driven by copper catalysis. However, significant studies have been made in Ullmann-type coupling reactions, particularly in the formation of biaryl structures, leading to more sustainable and efficient synthetic pathways. Recent research has concentrated on devising innovative catalytic systems, including palladium, gold, and nickel nanoparticles, and bimetallic species, to surmount the limitations of conventional copper catalysts. These advancements have broadened the range of substrates and enhanced reaction efficiency under gentler conditions, in line with the principles of green chemistry. Mechanistic studies have been instrumental in these developments, particularly focusing on the nonchain single-electron transfer (SET) mechanism. Additionally, the use of recyclable heterogeneous catalysts has mitigated the stringent reaction conditions associated with the original Ullmann reaction. As research continues to evolve, asymmetric Ullmann coupling is anticipated to become a key tool in the synthesis of complex natural products and heterocyclic systems pertinent to medicinal chemistry. This review aims to cover the recent developments in the Ullmann homocoupling reaction in sustainable and asymmetric catalytic systems for the synthesis of biaryl compounds.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770775","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

Ru(II)-catalyzed oxidative C-H spiroannulation of 4-arylquinazolin-2-ones with alkynes.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-03 DOI: 10.1039/d5ob00170f

Chidrawar Ajay, B Sridhar, B V Subba Reddy

引用次数: 0

Single-atom molecular editing: transformative advances in carbocyclic and heterocyclic frameworks.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-03 DOI: 10.1039/d5ob00272a

Parvin Moghimi, Hossein Sabet-Sarvestani, Vahid Moghimi, Nazanin Norozi-Shad, Michal Szostak

{"title":"Single-atom molecular editing: transformative advances in carbocyclic and heterocyclic frameworks.","authors":"Parvin Moghimi, Hossein Sabet-Sarvestani, Vahid Moghimi, Nazanin Norozi-Shad, Michal Szostak","doi":"10.1039/d5ob00272a","DOIUrl":"https://doi.org/10.1039/d5ob00272a","url":null,"abstract":"Single-atom editing has emerged as a transformative strategy in organic synthesis, enabling precise modification of carbocyclic and heterocyclic frameworks by selectively targeting single atoms. These frameworks are crucial backbones of pharmaceuticals, agrochemicals, and advanced materials, making this approach powerful for organic chemists. In drug discovery and natural product synthesis, single-atom editing diversifies molecular scaffolds and tailors molecular properties to enhance pharmacological activity. In heterocyclic synthesis, this approach enables controlled heteroatom substitution, addition or deletion in an unprecedented and highly selective manner compared to traditional methods. Recent advances in transition-metal catalysis, organocatalysis, photoredox catalysis, and heterocycle-to-heterocycle metamorphosis have expanded the versatility of single-atom editing, enabling the synthesis of various carbocyclic and heterocyclic compounds. Principally, this approach has been exploited to design new architectures that are not easily accessible by other methods and to establish major improvements in the synthesis of known scaffolds, providing more efficient and sustainable routes towards large-scale chemical synthesis. This review overviews recent advances, focusing on carbocyclic and heterocyclic frameworks, and is organized by key single-atom editing strategies, such as ring contractions, atom deletions, ring expansions, and atom insertions. The review highlights key transformations like Favorskii and Wolff rearrangements, alongside modern photochemical and transition-metal-catalyzed processes, to provide a broad overview of synthetic applications and inspire further advancements in targeted molecular edits.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770701","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

Organocatalytic cyclization-rearrangement cascade reaction: asymmetric construction of γ-lactams.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-03 DOI: 10.1039/d5ob00010f

Sheng-Feng Wu, Zhi-Yuan Wang, Xing-Wen Sun

引用次数: 0

Mn-catalyzed oxo-alkylation of 1,2,4-triazine-3,5(2H,4H)-diones with cyclic alkanols via oxidative cross-dehydrogenative coupling.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00098j

Qianqian Liang, Shuomeng Bai, Yushi Tan, Hong-Yu Zhang, Yuecheng Zhang, Jiquan Zhao

引用次数: 0

Investigations into the N-dealkylation reaction of protected chelating agents.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00114e

Jonathan Martinelli, Enrico Martorana, Angelo Marcotrigiano, Lorenzo Tei

{"title":"Investigations into the N-dealkylation reaction of protected chelating agents.","authors":"Jonathan Martinelli, Enrico Martorana, Angelo Marcotrigiano, Lorenzo Tei","doi":"10.1039/d5ob00114e","DOIUrl":"https://doi.org/10.1039/d5ob00114e","url":null,"abstract":"To comply with the specific requirements for the coordination of a certain metal ion, it is often necessary to decrease the substitution degree on the nitrogen atoms of well-known poly(aminocarboxylate) ligands used as chelators for the preparation of diagnostic or therapeutic probes. The procedures used so far to prepare such partially-alkylated compounds involve steps that suffer from product loss or the need to introduce protection/deprotection reactions, consequently lowering the final yield. The application of an N-dealkylation reaction to an exhaustively-substituted precursor could in principle allow to achieve the same result in fewer steps and therefore with higher yields. Dealkylation reactions have been known since the early 1900s, but they have never been exploited for such a purpose. We investigated the applicability of the simple iron-Polonovski N-dealkylation reaction to obtain a library of useful ligands starting from the tert-butyl-protected derivatives of chelators widely used in the biomedical fields such as CDTA, EDTA, NOTA, AAZTA and PCTA. The preparation of partially-alkylated ligands has already been reported in the literature but with several drawbacks and possible improvements. In most of the examples reported, it was found that the reaction occurred in an easy and straightforward way by only using an excess of oxidizing agent that was sufficient to convert the N-oxide into the N-dealkylated product without the need for a reducing agent.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143762768","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

Enhanced ester dechloroacetylation through transesterification with trimethoxyborane.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00255a

Sheng Zhang, Xiangrong Wang, Renhua Li, Zhangrong Lou, Haoyun Zhan, Masahiko Yamaguchi

引用次数: 0

Transition metal- and oxidant-free [3 + 2] cycloaddition of N-amino(iso)quinolinium salts with vinyl acetate as an acetylene surrogate.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00289c

Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge, Hang Cong

引用次数: 0

Stereoselective synthesis of the pyran subunit of portentol.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00235d

Tan Hoang Luu, Florian Heppner, Johal Ruiz, Dirk Menche

引用次数: 0

Electrochemically promoted tandem cyclization of functionalized methylenecyclopropanes: synthesis of tetracyclic benzazepine derivatives.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00238a

Min Li, Yin Wei, Min Shi

引用次数: 0