[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"doc-seo-450023-105":3,"detail-sidebar-cat-0-en-105":80,"doc-detail-450023-en":130},{"code":4,"msg":5,"data":6},0,"ok",{"site_id":7,"language":8,"slug":9,"title":10,"keywords":11,"description":12,"schema_data":13,"social_meta":73,"head_meta":75,"extra_data":77,"updated_unix":79},105,"en","cis-diuoromethyl-hetarylative-dearomatization-by-a-radical-docking-migration-cascade-chemical-science-edge-article","Cis-difluoromethyl hetarylative dearomatization by a radical docking-migration cascade - Chemical Science EDGE ARTICLE","","Despite progress in dearomatization reactions, achieving uncyclized dearomatization to form thermodynamically unstable 1,2-cis-products remains unresolved. A novel uncyclized cis-selective approach is presented using a radical docking-migration cascade under mild photochemical conditions, incorporating CF2H and a hetaryl group into indoline backbones. Broad indole scope is compatible, and the method also applies to benzothiophenes, furans, thiophenes, and selected PAHs without photosensitizers. DFT calculations rationalize regioselectivity and cis stereoselectivity.",{"@graph":14,"@context":72},[15,34,55],{"@type":16,"itemListElement":17},"BreadcrumbList",[18,23,27,31],{"item":19,"name":20,"@type":21,"position":22},"https://docshare.wps.com","Home","ListItem",1,{"item":24,"name":25,"@type":21,"position":26},"https://docshare.wps.com/document/","Document",2,{"item":28,"name":29,"@type":21,"position":30},"https://docshare.wps.com/document/research-report/","Research & Report",3,{"item":32,"name":10,"@type":21,"position":33},"https://docshare.wps.com/document/cis-diuoromethyl-hetarylative-dearomatization-by-a-radical-docking-migration-cascade-chemical-science-edge-article/450023/",4,{"url":32,"name":10,"@type":35,"image":36,"author":41,"headline":10,"publisher":44,"fileFormat":47,"inLanguage":8,"description":12,"dateModified":48,"datePublished":49,"encodingFormat":47,"isAccessibleForFree":50,"interactionStatistic":51},"DigitalDocument",{"url":37,"@type":38,"width":39,"height":40},"https://docshare.wps.com/thumbnails/cis-diuoromethyl-hetarylative-dearomatization-by-a-radical-docking-migration-cascade-chemical-science-edge-article/450023.png","ImageObject",300,407,{"name":42,"@type":43},"Logic","Person",{"url":19,"name":45,"@type":46},"DocShare","Organization","application/pdf","2026-10-02","2026-09-30",true,{"@type":52,"interactionType":53,"userInteractionCount":26},"InteractionCounter",{"@type":54},"ViewAction",{"@type":56,"mainEntity":57},"FAQPage",[58,64,68],{"name":59,"@type":60,"acceptedAnswer":61},"What problem does the study address in dearomatization chemistry?","Question",{"text":62,"@type":63},"The work targets the unresolved challenge of achieving uncyclized dearomatization to produce thermodynamically unstable 1,2-cis-products.","Answer",{"name":65,"@type":60,"acceptedAnswer":66},"How does the proposed method achieve cis-selective uncyclized dearomatization?",{"text":67,"@type":63},"It uses a radical docking-migration cascade under mild photochemical conditions to incorporate CF2H and a hetaryl group into indoline backbones with cis selectivity.",{"name":69,"@type":60,"acceptedAnswer":70},"Does the reaction require a photosensitizer or catalyst?",{"text":71,"@type":63},"No photosensitizer is required; the photochemical reaction proceeds efficiently under blue light conditions without a photocatalyst.","https://schema.org",{"og:url":32,"og:type":74,"og:title":10,"og:site_name":45,"og:description":12},"article",{"robots":76,"canonical":32},"index,follow",{"doc_id":78,"site_id":7},450023,1790917979,{"code":4,"msg":81,"data":82},"success",[83,87,91,95,100,105,110,114,119,122,126],{"id":22,"doc_module":4,"doc_module_name":25,"category_name":84,"show_sort_weight":85,"slug":86},"Story & Novel",90,"story-novel",{"id":26,"doc_module":4,"doc_module_name":25,"category_name":88,"show_sort_weight":89,"slug":90},"Literature",80,"literature",{"id":33,"doc_module":4,"doc_module_name":25,"category_name":92,"show_sort_weight":93,"slug":94},"Exam",70,"exam",{"id":96,"doc_module":4,"doc_module_name":25,"category_name":97,"show_sort_weight":98,"slug":99},5,"Comic",60,"comic",{"id":101,"doc_module":4,"doc_module_name":25,"category_name":102,"show_sort_weight":103,"slug":104},6,"Technology",50,"technology",{"id":106,"doc_module":4,"doc_module_name":25,"category_name":107,"show_sort_weight":108,"slug":109},7,"Healthcare",40,"healthcare",{"id":111,"doc_module":4,"doc_module_name":25,"category_name":29,"show_sort_weight":112,"slug":113},8,30,"research-report",{"id":115,"doc_module":4,"doc_module_name":25,"category_name":116,"show_sort_weight":117,"slug":118},9,"Religion & Spirituality",20,"religion-spirituality",{"id":117,"doc_module":4,"doc_module_name":25,"category_name":120,"show_sort_weight":117,"slug":121},"World Cup","world-cup",{"id":123,"doc_module":4,"doc_module_name":25,"category_name":124,"show_sort_weight":123,"slug":125},10,"Lifestyle","lifestyle",{"id":127,"doc_module":4,"doc_module_name":25,"category_name":128,"show_sort_weight":96,"slug":129},19,"General","general",{"code":4,"msg":81,"data":131},{"doc_id":78,"user_id":132,"nickname":42,"user_avatar":133,"doc_module":4,"category_id":111,"category_name":29,"doc_title":10,"doc_description":12,"doc_content":134,"file_id":135,"file_url":136,"file_type":137,"file_size":138,"view_count":26,"is_deleted":4,"is_public":22,"is_downloadable":22,"audit_status":22,"page_count":106,"language":139,"language_code":8,"site_id":7,"html_lang":8,"table_of_contents":140,"faqs":141,"seo_title":142,"seo_description":12,"update_tm":143,"read_time":144},1099513958762,"https://ap-avatar.wpscdn.com/avatar/1000023916a998db790?x-image-process=image/resize,m_fixed,w_180,h_180&k=1784791008015729253","Chemical Science  \nEDGE ARTICLE  \nCite this: DOI: 10 .1039/d5sc07904g  \nAll publication charges for this article have been paid for by the Royal Society of Chemistry  \nReceived 13th October 2025 Accepted 6th November 2025 DOI: 10.1039/d5sc07904g  \n[rsc.li/chemical-science](rsc.li/chemical-science)  \nCis-difluoromethyl hetarylative dearomatization by a radical docking-migration cascade  \nJie Wang,ab Hao Kang,a Shan Yang,a Zhu Cao,a Xiangyang Chen  *a and Chen Zhu  *ab  \nDespite the significant advances in dearomatization reactions, the challenge of achieving uncyclizeddearomatization to produce thermodynamically unstable 1,2-cis-products remains unresolved. Here, we present a novel approach for uncyclized cis-selective dearomatization reaction via a radical dockingmigration cascade. The reaction proceeds under mild photochemical conditions, simultaneously incorporating a CF2 H and a hetaryl group into indoline backbones. A wide range of indoles with diverse functional groups are compatible with the reaction. Furthermore, this method is also suitable for the dearomatization of benzothiophenes, furans, thiophenes and a few polycyclic aromatic hydrocarbons. This protocol features excellent selectivities, broad product diversity, and does not require photosensitizers. DFT calculations rationalize the observed regioselectivities for various heteroarenes and cis-stereoselectivities.  \nIntroduction  \nHeteroarenes are predominant moieties in numerous biologically active compounds, but their 􀀁at structural features o􀀁en cause the problem of poor solubility and metabolic instability,1 thus increasing the demand for an “escape from 􀀁atland”imperative for medicinal chemists.2 The dearomatization reaction represents a straightforward approach to convert planar heteroarenes into three-dimensional heterocyclic frameworks, providing more space for new drug discovery and structural modi􀀃cation of drug molecules.3 In this scenario, the last few decades have witnessed great progress in the 􀀃eld of radicalmediated dearomatization of heteroarenes,4 where indole serves as one of the most privileged precursors, giving rise to valuable indoline scaffolds that are abundant in natural products and drugs (Fig. 1A) . Among these efforts, the indoles with pendant aliphatic alkene or halide capable of generating an alkyl radical are frequently utilized, engaging in kinetically favoured intramolecular cyclization (Fig. 1B) .5 Moreover, intermolecular approaches proceed mainly via thermodynamically preferred trans-difunctionalization6 or [2 + 2] photocycloaddition.7 Nevertheless, the uncyclized dearomatization of  \naFrontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. E-mail: chzhu@ [sjtu.edu.cn](sjtu.edu.cn); [chenxiangyang@sjtu.edu.cn](chenxiangyang@sjtu.edu.cn)  \nbKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China  \nindoles leading to unusual and thermodynamically less stable cis-products remains unmet.  \nThe radical docking-migration cascade is proving to bea robust strategy for the structural modi􀀃cation of organic molecules.8 Nevertheless, its versatility has only been demonstrated in the conversion of alkenes and alkynes.9 We conceive to explore the feasibility of using it to address the elusive dearomative cis-difunctionalization. Here we disclose the proofof-principle studies. The uncyclized radical dearomatization of indoles, leading to cis-disubstituted indolines, is accomplished for the 􀀃rst time (Fig. 1C) . The reaction is facilitated by visiblelight irradiation, albeit in the absence of a photocatalyst. Besides indoles, this protocol can also be adapted to other electron-","cbCaii8dBDRUeGco","https://ap.wps.com/l/cbCaii8dBDRUeGco","pdf",1571248,"English","# Introduction\n## Dearomatization demand in medicinal chemistry\n## Radical-mediated dearomatization and limitations\n## Proposed radical docking-migration strategy\n# Results and discussion\n## Optimization using N-benzyl indole and sulfone reagent\n## Control experiments and role of light/additives/water\n## Substrate scope for indoles and extension to other heteroarenes","[{\"question\":\"What problem does the study address in dearomatization chemistry?\",\"answer\":\"The work targets the unresolved challenge of achieving uncyclized dearomatization to produce thermodynamically unstable 1,2-cis-products.\"},{\"question\":\"How does the proposed method achieve cis-selective uncyclized dearomatization?\",\"answer\":\"It uses a radical docking-migration cascade under mild photochemical conditions to incorporate CF2H and a hetaryl group into indoline backbones with cis selectivity.\"},{\"question\":\"Does the reaction require a photosensitizer or catalyst?\",\"answer\":\"No photosensitizer is required; the photochemical reaction proceeds efficiently under blue light conditions without a photocatalyst.\"}]","Cis-difluoromethyl hetarylative dearomatization by a radical docking-migration cascade - Chemical Science EDGE ARTICLE | PDF",1790731847,18]