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Ruthenium‐Catalyzed Regioselective Tandem Cycloisomerization/Diels‐Alder Reaction of 1,7‐Enynes 钌催化的 1,7-炔的区域选择性串联环异构化/Diels-Alder 反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-21 DOI: 10.1002/adsc.202401157
Ravichandran Logeswaran, Masilamani Jeganmohan
{"title":"Ruthenium‐Catalyzed Regioselective Tandem Cycloisomerization/Diels‐Alder Reaction of 1,7‐Enynes","authors":"Ravichandran Logeswaran, Masilamani Jeganmohan","doi":"10.1002/adsc.202401157","DOIUrl":"https://doi.org/10.1002/adsc.202401157","url":null,"abstract":"A ruthenium‐catalyzed methodology for regioselective cycloisomerization and tandem Diels‐Alder reactions of 1,7‐enynes has been described, enabling the versatile synthesis of diverse polycyclic heterocycles with four stereocenters. This stereoselective protocol demonstrates excellent compatibility with various substituted enynes and alkenes, yielding products in 46–90% yields while tolerating a wide range of functional groups, including esters, ketones, and halides. Notably, the reaction with naphthoquinones retains the moiety in the final product, which acts as essential core structures in various natural products and bioactive compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"253 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142679092","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Difuropyridines from Chitin-Derived 3-Acetamidofuran and their Application to Photocatalytic Reactions 从甲壳素衍生的 3-乙酰氨基呋喃合成二呋啶类化合物及其在光催化反应中的应用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-18 DOI: 10.1002/adsc.202401164
Haifeng Gan, Peipei Ma, Taixiang Yang, Fei Cao, Jianliang Zhu
{"title":"Synthesis of Difuropyridines from Chitin-Derived 3-Acetamidofuran and their Application to Photocatalytic Reactions","authors":"Haifeng Gan, Peipei Ma, Taixiang Yang, Fei Cao, Jianliang Zhu","doi":"10.1002/adsc.202401164","DOIUrl":"https://doi.org/10.1002/adsc.202401164","url":null,"abstract":"<p>Difuropyridines have been prepared from aldehydes and chitin-derived 3-acetamidofuran (3AF) under acid-catalyzed conditions. Difuropyridines were comprehensively synthesized for the first time. The synthesized difuropyridines can be applied to prepare fluorescent probe analogs or catalyze decarboxylative reactions as photocatalysts.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665560","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
The Chemistry of α-Enolizable Alkynones: a Comprehensive Review 可烯化的α-炔酮化学：全面回顾
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-18 DOI: 10.1002/adsc.202401312
Sofia Karnakova, Marina Dvorko, Dmitrii Shabalin
{"title":"The Chemistry of α-Enolizable Alkynones: a Comprehensive Review","authors":"Sofia Karnakova, Marina Dvorko, Dmitrii Shabalin","doi":"10.1002/adsc.202401312","DOIUrl":"https://doi.org/10.1002/adsc.202401312","url":null,"abstract":"This comprehensive review summarizes the published literature data concerning the chemistry of α-enolazible alkynones, also denoted aliphatic or C-H active alkynones, where an alkyl group is adjacent to the carbonyl function, from the first example in 1949 to the present day. Starting from a historical perspective, the reader will be introduced to the recent achievements and future challenges in this field. The review covers around 100 references.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"249 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142670394","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Synergistic Palladium/Silver/Ligand Catalysis for C−H Alkenylation of 2,1,3-Benzofused Heterodiazoles 钯/银/配体协同催化 2,1,3-苯并二唑的 C-H 烯化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-18 DOI: 10.1002/adsc.202401139
Siyeon Jeong, Chaerin Lee, Jung Min Joo
{"title":"Synergistic Palladium/Silver/Ligand Catalysis for C−H Alkenylation of 2,1,3-Benzofused Heterodiazoles","authors":"Siyeon Jeong, Chaerin Lee, Jung Min Joo","doi":"10.1002/adsc.202401139","DOIUrl":"https://doi.org/10.1002/adsc.202401139","url":null,"abstract":"<p>The combination of palladium and silver complexes has emerged as a bimetallic catalytic system in C−H activation, frequently outperforming palladium-only systems. Beyond the conventional roles of silver (I) salts serving as oxidants, halide scavengers, and Lewis acids, Pd−Ag bimetallic synergism has been shown to facilitate C−H cleavage. In this study, we explore the incorporation of a pyrazolopyridone (PzPyOH) ligand into a Pd−Ag bimetallic catalytic system, which together promote both C−H cleavage and migratory insertion processes. This synergistic approach enables dehydrogenative C−H alkenylations at the C4 position of 2,1,3-benzothiadiazole, 2,1,3-benzoxadiazole, and 2,1,3-benzotriazole with alkenes. These results demonstrate the potential of combining novel ligands with heterobimetallic systems to facilitate other elementary steps beyond C−H cleavage, suggesting their broader applicability in C−H functionalization.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"8 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665559","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Functionalized Benzo[f]chromanes and Hydroxyalkyl Naphthols: Catalytic Coupling of Naphthols and Allylic Alcohols 功能化苯并[f]色烷和羟基烷基萘酚的合成：萘酚和烯丙基醇的催化偶联
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-18 DOI: 10.1002/adsc.202401243
Raman Sankar, Chidambaram Gunanathan
{"title":"Synthesis of Functionalized Benzo[f]chromanes and Hydroxyalkyl Naphthols: Catalytic Coupling of Naphthols and Allylic Alcohols","authors":"Raman Sankar, Chidambaram Gunanathan","doi":"10.1002/adsc.202401243","DOIUrl":"https://doi.org/10.1002/adsc.202401243","url":null,"abstract":"Catalytic dearomatization of arenols is an uphill task that can serve as a powerful method to construct C-C bonds with unsaturated coupling partners. Herein, a simple and efficient strategy for coupling naphthols with allylic alcohols is reported. A single Ru(II) pincer catalyzed coupling of naphthols with primary allylic alcohols led to the formation of benzo(f)chromanes, whereas the use of secondary alcohols delivered the hydroxyalkyl naphthols. Broad substrate scope and good functional group tolerance are demonstrated. Notably, a high diastereoselectivity is attained on chromanes. Hydroxyalkyl naphthols are synthetically transformed into spiroethers, and dearomative bromination is achieved on chromanes. Mechanistic studies revealed the involvement of tandem reactions, a formal O-H bond activation of allylic alcohols by an active catalyst via amine-amide metal-ligand cooperation provided α-β, unsaturated carbonyl intermediates, which further underwent 1,4 conjugate addition with dearomatized naphthols. One of the crucial intermediates, naphthyl radical, is elucidated by EPR studies and trapped using a radical scavenger. Liberated hydrogen and water molecules are the only byproducts in these transformations.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142670393","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Recent Advances in Organocatalytic Asymmetric Synthesis of Bicyclo[3.3.1]nonane Frameworks 双环[3.3.1]壬烷框架的有机催化不对称合成的最新进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-16 DOI: 10.1002/adsc.202401158
Rong-Rong Ma, Bo-Yang Liu, Lei Yan, Jun-Bing Lin, Peng-Fei Xu
{"title":"Recent Advances in Organocatalytic Asymmetric Synthesis of Bicyclo[3.3.1]nonane Frameworks","authors":"Rong-Rong Ma, Bo-Yang Liu, Lei Yan, Jun-Bing Lin, Peng-Fei Xu","doi":"10.1002/adsc.202401158","DOIUrl":"https://doi.org/10.1002/adsc.202401158","url":null,"abstract":"The bicyclo[3.3.1]nonane ring represents an attractive yet challenging synthetic targets in the field of organic synthesis, especially in a stereocontrolled fashion. Over the past two decades, organocatalysis has emerged as an enabling technology for the facile construction of enantioenriched molecules with remarkably increasing complexity and diversity, and a myriad of chiral architectures containing bicyclo[3.3.1]nonane units were elegantly assembled through organocatalytic asymmetric transformations. This review summarizes recent advancements on this topic (mainly from 2010 to 2023), emphasizing the reaction types such as desymmetrization and cascade reactions of different prochiral starting materials toward various chiral bicyclo[3.3.1]nonanes as well as their aza, oxa and thio derivatives. Meanwhile, the synthetic strategy, reaction mechanism, substrate scope and synthetic applications of these catalytic reactions are also discussed. We hope that this review will motivate further development and application of organocatalytic asymmetric synthesis of bicyclo[3.3.1]nonane frameworks.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"75 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642606","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Rh(III)‐Catalyzed C‐H Cyclization of 2‐Arylbenzimidazoles with CF3‐Imidoyl Sulfoxonium Ylides and Further Sc(III)‐Catalyzed Deaminative Hydroxylation Rh(III)-Catalyzed C-H Cyclization of 2-Arylbenzimidazoles with CF3-Imidoyl Sulfoxonium Ylides and Further Sc(III)-Catalyzed Deaminative Hydroxylation
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-16 DOI: 10.1002/adsc.202401220
Juting Liao, Ruirui Zhai, Xiaoyang Gao, Hongliang Wu, Dulin Kong, Shuojin Wang, Xun Chen
{"title":"Rh(III)‐Catalyzed C‐H Cyclization of 2‐Arylbenzimidazoles with CF3‐Imidoyl Sulfoxonium Ylides and Further Sc(III)‐Catalyzed Deaminative Hydroxylation","authors":"Juting Liao, Ruirui Zhai, Xiaoyang Gao, Hongliang Wu, Dulin Kong, Shuojin Wang, Xun Chen","doi":"10.1002/adsc.202401220","DOIUrl":"https://doi.org/10.1002/adsc.202401220","url":null,"abstract":"An efficient Rh(III)‐catalyzed C‐H bond activation/cyclization of 2‐arylbenzimidazoles with CF3‐imidoyl sulfoxonium ylides has been achieved, yielding diverse CF3‐ and amino‐disubstituted 5,6‐dihydrobenzoimidazo[2,1‐a]isoquinolines, which could undergo a deaminative hydroxylation to access CF3‐ and hydroxy‐disubstituted 5,6‐dihydrobenzoimidazo[2,1‐a]isoquinolines under Sc(OTf)3 catalyst. This developed strategy features easily available starting materials, broad substrate scope, ready scalability and high efficiency. Moreover, the antitumor activities of selected products against some human cancer cell lines were also investigated, and the results indicated that several products show the effective antiproliferative activities.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"36 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642947","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Tetrahydro-β-carbolines via Cascade Sigmatropic Rearrangements 通过级联西格玛式重排合成四氢-β-羰基化合物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-13 DOI: 10.1002/adsc.202401189
Daiki Oka, Tomomi Ohtsuka, Ken-ichi Takao, Akihiro Ogura
{"title":"Synthesis of Tetrahydro-β-carbolines via Cascade Sigmatropic Rearrangements","authors":"Daiki Oka, Tomomi Ohtsuka, Ken-ichi Takao, Akihiro Ogura","doi":"10.1002/adsc.202401189","DOIUrl":"https://doi.org/10.1002/adsc.202401189","url":null,"abstract":"We have developed a synthesis for tetrahydro-β-carbolines involving cascade sigmatropic rearrangements. The substrates were conveniently prepared from parent anilines via a [2,3]-sigmatropic rearrangement and cyanomethylation. Silver-mediated decyanation afforded the corresponding iminium cation, which underwent a cascade consisting of an aza-Cope rearrangement, an aza-oxa-Cope rearrangement, an aromatization, and a Pictet–Spengler reaction, and tetrahydro-β-carbolines were obtained as the single product. The reaction involved seven bond scissions and four bond formations and was triggered by a single reagent.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609892","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
NaHCO3-promoted Formal [4+3] Annulation of Salicylaldehydes with Isoquinolinium Salts Accessing Isoquinoline-fused Benzo[f][1,3]oxazepines NaHCO3 促进水杨醛与异喹啉盐的正规 [4+3] 连接，获得异喹啉融合的苯并[f][1,3]氧氮杂卓
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-13 DOI: 10.1002/adsc.202401295
Qiang Tang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Xiaochun Jiang, Shizhang Ling, Yongjia Shang, Xinwei He
{"title":"NaHCO3-promoted Formal [4+3] Annulation of Salicylaldehydes with Isoquinolinium Salts Accessing Isoquinoline-fused Benzo[f][1,3]oxazepines","authors":"Qiang Tang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Xiaochun Jiang, Shizhang Ling, Yongjia Shang, Xinwei He","doi":"10.1002/adsc.202401295","DOIUrl":"https://doi.org/10.1002/adsc.202401295","url":null,"abstract":"A concise and practical sustainable strategy for modular access to isoquinoline-fused benzo[f][1,3]oxazepine derivatives through a formal [4+3] annulation of commercially available salicyaldehydes with isoquinolinium salts has been developed. The reactions proceeded through the formation of two new bonds (C=C and C-O) and a seven-membered heterocyclic ring in one pot. Remarkably, use of simple NaHCO3 as a mild base, open atmosphere, nonhazardous reagents, nice functional group tolerance, and easily scale up are added characteristics to this approach. A wide range of substrates are compatible with this mild reaction system, thereby proving a facile and reliable protocol for constructing a benzo[f][1,3]oxazepine skeletons.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"72 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609891","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bidentate NHC‐Containing Ligands for Copper Catalysed Synthesis of Functionalised Diaryl Ethers 铜催化合成功能化二元醚的双齿 NHC 配体
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-12 DOI: 10.1002/adsc.202400909
Ethan M. Richards, Luis Casarrubios, Jarryl M. D’Oyley, Henry S. Rzepa, Andrew White, Kristin Goldberg, Frederick W. Goldberg, James Bull, Silvia Díez-González
{"title":"Bidentate NHC‐Containing Ligands for Copper Catalysed Synthesis of Functionalised Diaryl Ethers","authors":"Ethan M. Richards, Luis Casarrubios, Jarryl M. D’Oyley, Henry S. Rzepa, Andrew White, Kristin Goldberg, Frederick W. Goldberg, James Bull, Silvia Díez-González","doi":"10.1002/adsc.202400909","DOIUrl":"https://doi.org/10.1002/adsc.202400909","url":null,"abstract":"Diaryl and heteroaryl ethers are important and common motifs in drug discovery and agrochemicals. Here we present a catalytic system for the copper catalysed arylation of phenols with aryl halides. Bidentate N‐heterocyclic carbene ligands provide a well‐defined catalytic system that enable low loading of copper in effective coupling reactions (0.5 mol% Cu or lower). The reaction scope of aryl iodides and aryl bromides is developed, that is tolerant of functional groups and a library of biaryl ethers with lead‐like properties is prepared. The presence of excess ligand (in a 1:3 ratio) is shown to be optimal to prevent catalyst degradation, presumably by avoiding decomplexation of the ligand. This is also supported by the catalytic results obtained with pre‐formed copper complexes. The kinetics of the reaction are examined and shown to be first order in copper, supportive of a well‐defined catalyst species, first order in phenol and aryl iodide, and zero order in base under the developed conditions. Computational studies performed using Minnesota MN15‐L parametrisation method support an oxidative addition–reductive elimination pathway. Reductive elimination would be turnover limiting and occurr through an intimate ion pair intermediate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"80 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142599592","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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