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Direct Synthesis of 3,4‐Disubstituted Quinolines and 2‐Acylquinolines from Amines and Epoxides 从胺和环氧化物直接合成 3,4-二取代喹啉和 2-酰基喹啉
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202401055
Xueyan Lv , Shichen Li , Shuai Fang , Xiaotian Wu , Bingchuan Yang , Chen Ma
{"title":"Direct Synthesis of 3,4‐Disubstituted Quinolines and 2‐Acylquinolines from Amines and Epoxides","authors":"Xueyan Lv ,&nbsp;Shichen Li ,&nbsp;Shuai Fang ,&nbsp;Xiaotian Wu ,&nbsp;Bingchuan Yang ,&nbsp;Chen Ma","doi":"10.1002/adsc.202401055","DOIUrl":"10.1002/adsc.202401055","url":null,"abstract":"<div><div>Herein, we present a protocol starting from styrene oxide reacting with <em>o</em>‐acylaniline and <em>o</em>‐alkenylaniline derivatives to obtain 3,4‐disubstituted quinoline and 2‐acylquinoline derivatives, respectively, in 32–92% yields under specific conditions. Preliminary research outcomes underscore the versatility of our approach, as exemplified by its scalability for large‐scale synthesis, downstream derivatization, and the characteristic properties manifested by the modified molecules.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202401055"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487055","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 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 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 ,&nbsp;Chaerin Lee ,&nbsp;Jung Min Joo","doi":"10.1002/adsc.202401139","DOIUrl":"10.1002/adsc.202401139","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202401139"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","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
Tandem Photocatalyst‐Free Visible Light Aryl Azidation‐Intramolecular C−H Amination: One‐Pot Access to Carbazoles and Indoles from Areneazo‐2‐(2‐nitro)propanes 串联无光催化剂可见光芳基叠氮化-分子内C - H胺化：从2-（2-硝基）丙烷中获得咔唑和吲哚的一锅方法
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202401333
Dilip V. Patil , Rahulkumar Patel , Shinobu Takizawa , Hun Y. Kim , Kyungsoo Oh
{"title":"Tandem Photocatalyst‐Free Visible Light Aryl Azidation‐Intramolecular C−H Amination: One‐Pot Access to Carbazoles and Indoles from Areneazo‐2‐(2‐nitro)propanes","authors":"Dilip V. Patil ,&nbsp;Rahulkumar Patel ,&nbsp;Shinobu Takizawa ,&nbsp;Hun Y. Kim ,&nbsp;Kyungsoo Oh","doi":"10.1002/adsc.202401333","DOIUrl":"10.1002/adsc.202401333","url":null,"abstract":"<div><div>The visible light‐induced one‐pot tandem photolysis of areneazo‐2‐(2‐nitro)propanes was achieved to give carbazole and indole derivatives. The aryl azidation followed by an intramolecular C−H amination smoothly proceeded under visible light irradiation without any photocatalyst, demonstrating the synthetic versatility of areneazo‐2‐(2‐nitro)propanes. The <em>in situ</em> generation of aryl azide intermediates was executed under mild visible light photolysis conditions, showcasing the synthetic versatility of areneazo‐2‐(2‐nitro)propanes, a safe alternative of diazonium salts.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202401333"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810022","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
First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐One O‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles 第一溴化物催化2 -炔- 1 - 1 - O -甲基肟的硒化使4 -硒化异恶唑的合成成为可能
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202401477
Jinhui Cai , Zhouting Zeng
{"title":"First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐One O‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles","authors":"Jinhui Cai ,&nbsp;Zhouting Zeng","doi":"10.1002/adsc.202401477","DOIUrl":"10.1002/adsc.202401477","url":null,"abstract":"<div><div>A series of 3,5‐diaryl‐4‐selanylisoxazoles were synthesized in 56–97% yields (most cases&gt;80% yield), which was first accomplished via bromide‐catalyzed selenylation of 2‐alkyn‐1‐one <em>O</em>‐methyloximes using element Se and boronic acids as the selenyl source. Compared to traditional strategies, this method proceeded under simple catalytic system. Broad substrate scope, good functional group compatibility, metal‐free conditions, and easy operation was showed in this protocol. Additionally, this method was easily amendable to gram‐scale reaction and synthetic transformations. Furthermore, preliminary mechanistic experiments demonstrated that a radical pathway was possibly involved in this work.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202401477"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142961630","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
Dual C2 Synthon Strategy for the Synthesis of Pyrimidines: Copper‐Catalyzed Aerobic α,β‐C(sp3)−H Bond Difunctionalization of Tertiary Alkylamines 合成嘧啶的双 C2 合成策略：铜催化三级烷基胺的α,β-C(sp3)-H 键双官能化
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202400907
Ramachandra Reddy Putta , Junhwa Hong , Seung Hyun Choi , Jinwoo Lee , Honghui Lee , Seok Beom Lee , Suckchang Hong
{"title":"Dual C2 Synthon Strategy for the Synthesis of Pyrimidines: Copper‐Catalyzed Aerobic α,β‐C(sp3)−H Bond Difunctionalization of Tertiary Alkylamines","authors":"Ramachandra Reddy Putta ,&nbsp;Junhwa Hong ,&nbsp;Seung Hyun Choi ,&nbsp;Jinwoo Lee ,&nbsp;Honghui Lee ,&nbsp;Seok Beom Lee ,&nbsp;Suckchang Hong","doi":"10.1002/adsc.202400907","DOIUrl":"10.1002/adsc.202400907","url":null,"abstract":"<div><div>Herein, we describe a two‐component methodology developed for the synthesis of pyrimidine derivatives using tertiary alkylamines and amidines. Tertiary alkylamines serve as dual C2 synthons through copper‐catalyzed aerobic difunctionalization of the α,β−C(<em>sp</em><sup>3</sup>)−H bonds. The process operates under mild conditions and uses atmospheric oxygen as the oxidant. Notably, by this methodology yields up to 85% yields are obtained and a broad substrate scope is shown. Mechanistic studies indicate that the annulation proceeds <em>via</em> a radical‐mediated oxidation and C−N bond coupling process. This approach provides a pathway for synthesizing various heterocycles by employing tertiary alkylamines as dual C2 synthons.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202400907"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452581","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
Stereodivergent Synthesis of Chiral Hydrobenzofuranpyrrolidines by Catalytic Asymmetric Dearomative Cyclization and Controlled Epimerization 通过催化不对称二元环化和受控外延合成手性苯并呋喃吡咯烷
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202401194
Wei Liu , Yeting Huang , Ziqiang Dai , Min Yu , Xuangan Liu , Weijun Yao , Xiaoyu Han
{"title":"Stereodivergent Synthesis of Chiral Hydrobenzofuranpyrrolidines by Catalytic Asymmetric Dearomative Cyclization and Controlled Epimerization","authors":"Wei Liu ,&nbsp;Yeting Huang ,&nbsp;Ziqiang Dai ,&nbsp;Min Yu ,&nbsp;Xuangan Liu ,&nbsp;Weijun Yao ,&nbsp;Xiaoyu Han","doi":"10.1002/adsc.202401194","DOIUrl":"10.1002/adsc.202401194","url":null,"abstract":"<div><div>A methodology to access stereoisomeric sets of products bearing multiple stereogenic centers is still a significant challenge in asymmetric catalysis. We present herein our experimental studies on the stereodivergent synthesis of chiral hydrobenzofuran‐fused pyrrolidines with three stereogenic centers via organocatalytic asymmetric dearomative cyclization and epimerization process. Chiral bifunctional thiourea catalyst could successfully promote the enantioselective dearomatization cyclization of 2‐nitrobenzofurans with <em>o</em>‐hydroxy aromatic aldimines, which enabled the synthesis of (3<em>S</em>,3a<em>R</em>,8b<em>R</em>)‐hydrobenzofuran[3.2]pyrrolidines in 79–92% yields with &gt;20:1 stereoselectivities and 93–&gt;99% enantio‐selectivities. While catalytic amount of DBU could induce the direct intramolecular epimerization of (3<em>S</em>,3a<em>R</em>,8b<em>R</em>)‐hydrobenzofuran[3.2] pyrrolidines to its diastereomers (3<em>R</em>,3a<em>R</em>,8b<em>R</em>)‐hydrobenzofuran[3.2] pyrrolidines in 72–87% yields without loss of stereoselectivities. The mechanistic pathways of the epimerization process were investigated by a series of control experiments study. This work provides an alternative and forward solution for the stereodivergent preparation of functionalized pyrrolidines with potential bioactivities.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":"Article e202401194"},"PeriodicalIF":4.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486570","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
CuF2‐Catalyzed C‐N Cross‐Coupling of Aryl Silanes: Expanding the Scope of Chan‐Lam Type Reaction
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI: 10.1002/adsc.202401498
Vishal Talukdar, Siddhartha Paul, Krishanu Mondal, Parthasarathi Das
{"title":"CuF2‐Catalyzed C‐N Cross‐Coupling of Aryl Silanes: Expanding the Scope of Chan‐Lam Type Reaction","authors":"Vishal Talukdar, Siddhartha Paul, Krishanu Mondal, Parthasarathi Das","doi":"10.1002/adsc.202401498","DOIUrl":"https://doi.org/10.1002/adsc.202401498","url":null,"abstract":"An efficient copper‐catalyzed Chan–Lam type N‐arylation of various amides, sulfonamides, urea, azoles, and amines has been demonstrated using a CuF2/DMSO catalytic system with structurally diverse aryl(trimethoxy)silanes under base and ligand‐free conditions. This approach facilitates effective C‐N cross‐coupling with user‐friendly organosilicon reagents without requiring an external fluoride source. CuF2 serves a dual function as both a catalyst and a desilylating agent, facilitating the cleavage of the aryl‐silane bond. The process is compatible with a broad range of substrates, ensuring high efficiency and excellent functional group compatibility. Moreover, this protocol is proven to be valuable for late‐stage modification of amide and sulfonamide‐containing drug molecules, as well as for synthesizing agrochemicals.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"64 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435367","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
A Mild Reductant NHC‐ligated Borane for N‑Formylation of Amines with CO2 under Ambient Conditions 一种温和的 NHC 配位硼烷还原剂，用于在环境条件下用 CO2 对胺进行 N-甲酰化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-15 DOI: 10.1002/adsc.202401384
Wangyu Li, Shiwen Zhou, He Tang, Fengjian Chu, Hongru Feng, Yuan-Jiang Pan
{"title":"A Mild Reductant NHC‐ligated Borane for N‑Formylation of Amines with CO2 under Ambient Conditions","authors":"Wangyu Li, Shiwen Zhou, He Tang, Fengjian Chu, Hongru Feng, Yuan-Jiang Pan","doi":"10.1002/adsc.202401384","DOIUrl":"https://doi.org/10.1002/adsc.202401384","url":null,"abstract":"A convenient and efficient metal‐free protocol has been reported for formylation of various amines with carbon dioxide. This reaction could proceed under ambient conditions and show a broad substrate scope, encompassing primary amines, secondary amines, chiral amino acid esters and bioactive molecules. Furthermore, this method offers several advantages, including the preservation of substrate chirality, ease of separation and purification and the suitability of formic acid and formate salts as reactants in this reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"64 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418445","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
Cobalt/Salox‐catalyzed Stereoselective C‐H Functionalization: Enantioselective Construction of Axially Chiral Cyclic Phosphinamides with P‐Stereogenic Center
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-12 DOI: 10.1002/adsc.202500021
Bo Jiang, Hui Wang, Xiaobin Sun, Yiyang Qiao, Xiufang Xu, Zhiwei Miao
{"title":"Cobalt/Salox‐catalyzed Stereoselective C‐H Functionalization: Enantioselective Construction of Axially Chiral Cyclic Phosphinamides with P‐Stereogenic Center","authors":"Bo Jiang, Hui Wang, Xiaobin Sun, Yiyang Qiao, Xiufang Xu, Zhiwei Miao","doi":"10.1002/adsc.202500021","DOIUrl":"https://doi.org/10.1002/adsc.202500021","url":null,"abstract":"We describe a novel cobalt/salicyloxazoline (Salox) catalytic system for enantioselective C‐H functionalization, enabling the synthesis of P‐stereogenic and axially chiral cyclic phosphinic amides. Chiral Salox ligands, conveniently prepared in a single step from salicylonitriles and chiral amino alcohols, facilitated this transformation with excellent enantioselectivities (92‐99% ee) and moderate to good yields (31 examples, 45‐89%). Mechanistic studies implicate a cobalt (III/IV/II) catalytic cycle in the C‐H annulation process, providing valuable insights into the stereoselective reaction pathway.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393099","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 Iodine‐Mediated Radical Reactions
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-12 DOI: 10.1002/adsc.202401486
Wen Yang, Jian Guo, Samual Hee, Yu Chen
{"title":"Recent Advances in Iodine‐Mediated Radical Reactions","authors":"Wen Yang, Jian Guo, Samual Hee, Yu Chen","doi":"10.1002/adsc.202401486","DOIUrl":"https://doi.org/10.1002/adsc.202401486","url":null,"abstract":"Over the past two decades, iodine‐mediated free radical reactions have been extensively explored and employed in chemical transformations that complement traditional ionic reactions. In this review, we have updated the progress of the iodine‐mediated radical reactions in organic synthesis reported between 2015 and mid‐2024, and organized the reactions according to their mechanistic pathways. In general, the proposed mechanisms can be divided into four categories based on the radical initiation or its preceding steps, namely, (1) formation of a covalent X–I (X = C, N, S, Se) bond, which subsequently participates in a radical reaction; (2) formation of a noncovalent N•••I bond, which assists the homolyisis of the I–I bond; (3) formation of the key iodine radicals by visible‐light or heat induced homolysis of I2 or by electrochemical oxidation of iodide; (4) iodine induced peroxide decomposition via single electron transfer (SET) mechanism to generate alkoxy or alkyl peroxy radicals. We hope this review will provide readers with a comprehensive update on the iodine‐mediated radical reactions, thereby further inspiring more exciting advances in this emerging field.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393098","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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