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DFT Study on the Mechanistic Origin of the Distinct Reactivities of Three Iodine(III) Reagents in MIA‐Directed Pd‐Catalyzed C(sp3)–H Alkoxylation 三种碘（III）试剂在MIA定向Pd催化的C(sp3) -H烷氧基化中不同反应性机理的DFT研究
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70419
Peng‐Yu Liu , Rui‐Xia Sun , Qingsong Sun , Yu‐Peng He
{"title":"DFT Study on the Mechanistic Origin of the Distinct Reactivities of Three Iodine(III) Reagents in MIA‐Directed Pd‐Catalyzed C(sp3)–H Alkoxylation","authors":"Peng‐Yu Liu ,&nbsp;Rui‐Xia Sun ,&nbsp;Qingsong Sun ,&nbsp;Yu‐Peng He","doi":"10.1002/ajoc.70419","DOIUrl":"10.1002/ajoc.70419","url":null,"abstract":"<div><div>Hypervalent iodine(III) reagents are widely used in Pd‐catalyzed C─H functionalization, yet their efficacy varies dramatically with the acyloxy group. This DFT study elucidates the mechanistic origins of the reactivity differences among PhI(OAc)<sub>2</sub>, PhI(OCOCF<sub>3</sub>)<sub>2</sub>, and PhI(OPiv)<sub>2</sub> in a C(sp<sup>3</sup>)–H alkoxylation. All three systems are found to follow a unified pathway involving the oxidative addition of an acyloxy radical to a Pd(II) center, followed by concerted metalation‐deprotonation (CMD) for C─H cleavage and a final S<sub>N</sub>2‐type reductive elimination. PhI(OAc)<sub>2</sub> delivers the highest yield due to an optimal radical dissociation energy (17.9 kcal/mol) and the lowest CMD activation barrier (19.7 kcal/mol). In contrast, the strong electron‐withdrawing nature of the trifluoroacetoxy groups significantly elevates the radical dissociation energy of PhI(OCOCF<sub>3</sub>)<sub>2</sub> to 38.1 kcal/mol, rendering oxidant activation the rate‐determining step. For PhI(OPiv)<sub>2</sub>, the pivalate group's weak trans effect destabilizes the CMD step (21.2 kcal/mol). These findings provide a mechanistically grounded electronic rationale for acyloxy‐group effects in this MIA (2‐<strong>M</strong>ethoxy<strong>i</strong>mino<strong>a</strong>cyl)‐directed model alkoxylation system and may offer qualitative guidance for related Pd‐catalyzed C(sp<sup>3</sup>)–H alkoxylation reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70419"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753663","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Two‐Step Access to 4‐Aryl‐5‐Heteroarylpyrazoles via Palladium‐Catalyzed Sequential Transformations Using Palladium 1,4‐Migration Tool 利用钯1,4迁移工具通过钯催化的顺序转化两步获得4-芳基-5-杂芳基吡唑
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70383
Bo Lan , Thierry Roisnel , Henri Doucet
{"title":"Two‐Step Access to 4‐Aryl‐5‐Heteroarylpyrazoles via Palladium‐Catalyzed Sequential Transformations Using Palladium 1,4‐Migration Tool","authors":"Bo Lan ,&nbsp;Thierry Roisnel ,&nbsp;Henri Doucet","doi":"10.1002/ajoc.70383","DOIUrl":"10.1002/ajoc.70383","url":null,"abstract":"<div><div>Access to pyrazoles (hetero)arylated at both the C4 and C5 positions via palladium‐catalyzed C─H bond activation is generally challenging. This is due to the similar reactivity of these two positions, which often results in the formation of mixtures of C4‐, C5‐ and C4, C5‐(di)functionalized pyrazoles. The present report describes the synthesis of 4‐aryl‐5‐heteroarylpyrazoles through a novel method that involves Suzuki coupling of 1,2‐dihalobenzene with pyrazol‐4‐ylboronic acids, followed by palladium‐catalyzed C─H bond arylation. The key step in this methodology is the Pd 1,4‐migration, which occurs between the aryl and pyrazole rings in the C─H bond arylation catalytic cycle. This step regio‐selectively activates the C─H bond at the C5 position of the pyrazole ring. This pyrazole heteroarylation method exhibits a high level of tolerance to substituents on the benzene ring as well as a variety of heteroarenes. Furthermore, air‐stable catalysts and inexpensive bases were utilized in these reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70383"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147668006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Molecular Iodine Enabled Cascade Oxidation and Annulation for the Construction of Polycyclic 5‐aroyl‐5,6‐dihydropyrazolo[1,5‐c]Quinazolines 多环5-芳基-5,6-二氢吡唑啉[1,5-c]喹唑啉的分子碘激活级联氧化和环化制备
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70389
Swanand Vinayak Joshi , Samiksha Patil , Danaboina Srikanth , Arbaz Sujat Shaikh , Abdul Kalam , Nitesh Tamang , Rushikesh V. Suradkar , Amol G. Dikundwar , Venkata Madhavi Yaddanapudi , Srinivas Nanduri
{"title":"Molecular Iodine Enabled Cascade Oxidation and Annulation for the Construction of Polycyclic 5‐aroyl‐5,6‐dihydropyrazolo[1,5‐c]Quinazolines","authors":"Swanand Vinayak Joshi ,&nbsp;Samiksha Patil ,&nbsp;Danaboina Srikanth ,&nbsp;Arbaz Sujat Shaikh ,&nbsp;Abdul Kalam ,&nbsp;Nitesh Tamang ,&nbsp;Rushikesh V. Suradkar ,&nbsp;Amol G. Dikundwar ,&nbsp;Venkata Madhavi Yaddanapudi ,&nbsp;Srinivas Nanduri","doi":"10.1002/ajoc.70389","DOIUrl":"10.1002/ajoc.70389","url":null,"abstract":"<div><div>A practical, metal‐free, molecular iodine‐mediated one‐pot protocol has been developed for the construction of 5‐aroyl‐5,6‐dihydropyrazolo[1,5‐<em>c</em>]quinazolines from readily accessible aryl/heteroaryl acetophenones and 5‐(2‐aminophenyl)‐1<em>H</em>‐pyrazoles, thereby forming two new C‐N bonds. Notably, this represents the first report on the synthesis of 5‐aroyl‐substituted pyrazolo[1,5‐<em>c</em>]quinazolines, whereas all previously reported methods are limited to 5‐aryl analogues. The methodology exhibits broad substrate scope and functional group tolerance, extending beyond acetophenones to include phenylacetylenes, styrene, and 2‐hydroxyacetophenone, delivering the desired heterocycles in moderate to good yields. Further, benzyl alcohols serve as viable precursors under identical conditions to afford 5‐aryl‐5,6‐dihydropyrazolo[1,5‐<em>c</em>]quinazolines. The synthetic utility of the protocol is demonstrated by gram‐scale synthesis. The structure of a representative product <strong>3a</strong> was unambiguously determined by single‐crystal XRD. Mechanistic investigations, supported by HRMS studies, provide insight into the plausible reaction pathway.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70389"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147668438","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Enantioselective Aerobic Construction of C2‐Quaternary Indolin‐3‐ones by Gold/Chiral Amine Relay Catalysis 金/手性胺接力催化C2 -季吲哚啉- 3 -酮的有氧对映选择性构建
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70417
Geng Zhang , Si‐Ru Wang , Song‐Xiang Huang , Meng‐Meng Li , Shen‐Dong Ren , Zhen‐Yu Wang , Lan‐Jun Cheng , Xiang Wu
{"title":"Enantioselective Aerobic Construction of C2‐Quaternary Indolin‐3‐ones by Gold/Chiral Amine Relay Catalysis","authors":"Geng Zhang ,&nbsp;Si‐Ru Wang ,&nbsp;Song‐Xiang Huang ,&nbsp;Meng‐Meng Li ,&nbsp;Shen‐Dong Ren ,&nbsp;Zhen‐Yu Wang ,&nbsp;Lan‐Jun Cheng ,&nbsp;Xiang Wu","doi":"10.1002/ajoc.70417","DOIUrl":"10.1002/ajoc.70417","url":null,"abstract":"<div><div>This study describes an efficient and environmentally friendly strategy for the enantioselective synthesis of C2‐quaternary indolin‐3‐ones via a gold/<em>L</em>‐proline relay catalytic system using air as a sustainable oxidant. The reaction proceeds through a gold‐catalyzed cyclization of 2‐alkynyl arylazides to form a key 3<em>H</em>‐indol‐3‐one intermediates, followed by an <em>L</em>‐proline‐catalyzed asymmetric Mannich reaction with ketones. Under optimized conditions, the method affords a wide range of chiral 2,2‐disubstituted indolin‐3‐ones in moderate to good yields with excellent enantioselectivities (up to &gt;99% ee) and diastereoselectivities. The scope of both azide and ketone substrates was extensively explored, demonstrating broad functional group tolerance. Isotope labeling experiments confirmed that the carbonyl oxygen on the indole ring originates from water or acetone. This strategy offers a green and practical approach to accessing enantioenriched C2‐quaternary indolin‐3‐ones.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70417"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753618","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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‑Mediated Ortho‑C─H Halogenation of Arylaldehydes Enabled by a Transient Directing Group 铜介导的芳醛邻C─H卤化反应的瞬态导向基团
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70403
Kexue Xing , Jian Yang , Guiyuan Liu , Zijin Luo , Qingbo Ma , Xianghao Zhang , Chengrong Ding , Jinghui Lyu , Yiyong Zhao , Guofu Zhang
{"title":"Copper‑Mediated Ortho‑C─H Halogenation of Arylaldehydes Enabled by a Transient Directing Group","authors":"Kexue Xing ,&nbsp;Jian Yang ,&nbsp;Guiyuan Liu ,&nbsp;Zijin Luo ,&nbsp;Qingbo Ma ,&nbsp;Xianghao Zhang ,&nbsp;Chengrong Ding ,&nbsp;Jinghui Lyu ,&nbsp;Yiyong Zhao ,&nbsp;Guofu Zhang","doi":"10.1002/ajoc.70403","DOIUrl":"10.1002/ajoc.70403","url":null,"abstract":"<div><div>The transient directing group (TDG) strategy enables C─H functionalization without the need for pre‐installing and subsequently removing a directing group. In this study, we present a novel copper‐mediated, TDG‐promoted <em>ortho‐</em>C─H halogenation of arylaldehydes. This strategy employs an economical copper mediated in conjunction with a <em>β</em>‐amino acid derivative as the TDG, thereby achieving highly regioselective halogenation under mild conditions. The method demonstrates a wide substrate scope and exhibits a selectivity profile that is distinct from classical electrophilic aromatic substitution. Mechanistic studies have elucidated the existence of a key bromine radical intermediate and the involvement of a concerted metalation‐deprotonation (CMD) process.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70403"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Photocatalytic Dearomative Hydroxylation of 2‐aryl‐3‐aryl/Alkyl Indoles 可见光介导的2 -芳基- 3 -芳基/烷基吲哚的脱芳羟基化反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70391
Shubham Choudhari , Suchit Kumar Yadav , Prem P. Yadav
{"title":"Visible Light‐Mediated Photocatalytic Dearomative Hydroxylation of 2‐aryl‐3‐aryl/Alkyl Indoles","authors":"Shubham Choudhari ,&nbsp;Suchit Kumar Yadav ,&nbsp;Prem P. Yadav","doi":"10.1002/ajoc.70391","DOIUrl":"10.1002/ajoc.70391","url":null,"abstract":"<div><div>We have developed a visible‐light‐driven photocatalytic protocol for the efficient synthesis of 3‐hydroxyindolenines under mild reaction conditions. The transformation proceeds via a photocatalytic oxidative process mediated by chlorophyll, which functions as a sustainable, metal‐free, and environmentally benign photocatalyst. Upon irradiation with visible light, chlorophyll is photoexcited to its reactive excited state, enabling effective single‐electron transfer (SET) and/or energy‐transfer pathways that promote the oxidative functionalization of the indole framework. This reaction facilitates selective oxidation at the C3 position of indole substrates, leading to the formation of 3‐hydroxyindolenine derivatives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70391"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753734","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Bifunctionalization of Unactivated Alkenes for Synthesizing β‐Acetamido Selenides 铜催化非活化烯烃双官能化合成β-乙酰氨基硒
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70346
Juan Wang , Rui Huang , Changyuan Zhou , Pingping Tang , Chunru Cheng
{"title":"Copper‐Catalyzed Bifunctionalization of Unactivated Alkenes for Synthesizing β‐Acetamido Selenides","authors":"Juan Wang ,&nbsp;Rui Huang ,&nbsp;Changyuan Zhou ,&nbsp;Pingping Tang ,&nbsp;Chunru Cheng","doi":"10.1002/ajoc.70346","DOIUrl":"10.1002/ajoc.70346","url":null,"abstract":"<div><div>A direct and efficient acetylaminoselenylation reaction of unactivated alkenes is reported herein, utilizing acetonitrile as the nucleophile through a copper‐catalyzed redox process. This transformation features a broad substrate scope, excellent regioselectivity, and affords <em>β</em>‐acetamido selenide derivatives in moderate to high yields. Notably, the method employs cost‐effective copper catalysts and mild reaction conditions, addressing the limitations of existing synthetic routes for <em>β</em>‐acetamido selenides. These attributes make it a practical platform for constructing molecular scaffolds with potential biological and pharmaceutical relevance.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70346"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147585118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Access to Cyclobutanones by a Photoredox‐Catalyzed Deoxygenation/Wolff Rearrangement/Cycloadditions Cascade Reaction 光氧化还原催化脱氧/Wolff重排/环加成级联反应获得环丁酮
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70398
Hui Yang , Ying Lian , Yan Li , Wenhui Zhang , Shuqian Wang , Ni Yang , Biao Xu , Guoliang Lin , Zeyu Song , Guo Wei
{"title":"Access to Cyclobutanones by a Photoredox‐Catalyzed Deoxygenation/Wolff Rearrangement/Cycloadditions Cascade Reaction","authors":"Hui Yang ,&nbsp;Ying Lian ,&nbsp;Yan Li ,&nbsp;Wenhui Zhang ,&nbsp;Shuqian Wang ,&nbsp;Ni Yang ,&nbsp;Biao Xu ,&nbsp;Guoliang Lin ,&nbsp;Zeyu Song ,&nbsp;Guo Wei","doi":"10.1002/ajoc.70398","DOIUrl":"10.1002/ajoc.70398","url":null,"abstract":"<div><div>Novel synthesis of cyclobutanones is realized through a visible‐light catalyzed deoxygenation‐Wolff‐cycloaddition cascade reaction. Substituents of both electron‐donating and electron‐withdrawing properties can be well tolerated. This strategy provides a straightforward access to substituted cyclobutanones from readily available xF0x9Dx9BxBC‐diketones under mild conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70398"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147668563","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Insight Into the Substrate‐Based Influence on the Stereo‐ and Regioselectivity of the Intermolecular Oxidopyrylium (5 + 2) Cycloaddition Reaction 对分子间氧化吡啶（5 + 2）环加成反应立体选择性和区域选择性影响的底物研究
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70401
Beyza N. Yilmaz , Tatyana Popkova , Ryan P. Murelli
{"title":"Insight Into the Substrate‐Based Influence on the Stereo‐ and Regioselectivity of the Intermolecular Oxidopyrylium (5 + 2) Cycloaddition Reaction","authors":"Beyza N. Yilmaz ,&nbsp;Tatyana Popkova ,&nbsp;Ryan P. Murelli","doi":"10.1002/ajoc.70401","DOIUrl":"10.1002/ajoc.70401","url":null,"abstract":"<div><div>The oxidopyrylium (5 + 2) cycloaddition reaction provides rapid construction of complex bicyclic structures and has proven value within the synthetic organic chemistry community. However, the intermolecular variant of the reaction suffers from various documented challenges, one of which is often low regio‐ and stereoselectivity. We recently reported that oxidopyrylium ylides can react with methyl propiolate to yield 2:1 ylide:methyl propiolate “pincer” cycloadducts with high stereo‐ and regioselectivity. However, depending upon the nature of substitution on the ylide, different regio‐ and stereoisomers are formed. As a result, we found this discovery a valuable starting point for understanding the nuances that dictate the selectivity of oxidopyrylium cycloadditions and embarked on follow‐up studies. The following manuscript describes this work, which leverages a combination of computational and experimental studies to determine that the selectivity of oxidopyrylium pincer cycloadducts is governed by kinetics and is rationalized based upon both sterics and molecular orbital considerations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70401"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753733","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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/Photoredox‐Catalyzed Regioselective Hydroamination of 1,3‐Dienes With Free Amines 钴/光氧化还原催化1,3 -二烯与游离胺的区域选择性氢胺化
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI: 10.1002/ajoc.70411
Yukun Chen , Qi Meng , Dekai Li , Bei Chen , Ge Zhang , Qian Zhang
{"title":"Cobalt/Photoredox‐Catalyzed Regioselective Hydroamination of 1,3‐Dienes With Free Amines","authors":"Yukun Chen ,&nbsp;Qi Meng ,&nbsp;Dekai Li ,&nbsp;Bei Chen ,&nbsp;Ge Zhang ,&nbsp;Qian Zhang","doi":"10.1002/ajoc.70411","DOIUrl":"10.1002/ajoc.70411","url":null,"abstract":"<div><div>Allylic amines are ubiquitous motifs in pharmaceuticals, agrochemicals, and materials, yet direct access to regioisomeric variants remains limited. Here, we report a dual cobalt/photoredox catalytic platform that enables regioselective 1,4‐hydroamination of acyclic 1,3‐dienes. The transformation proceeds via a metal−hydride hydrogen atom transfer (MHAT) from a Co─H species, followed by a radical‐polar crossover nucleophilic amination process, which delivers (<em>E</em>)‐allylamines under mild conditions, with broad functional group tolerance, compatibility with complex molecules, and scalability that enables the incorporation of anilines and even more nucleophilic and basic dialkyl amines as feedstocks and expands the synthetic toolbox for alkene hydrofunctionalization.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 4","pages":"Article e70411"},"PeriodicalIF":2.7,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147753740","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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