Pub Date : 2025-12-10DOI: 10.1021/acs.orglett.5c04576
Weixin Xiao,Zhengyi Yi,Yong Liu,Lunyu Ou,Hongyun Li,Yue Zhang,Haijun Yang,Hua Fu
Synthesis of chiral eight-membered rings with high regioselectivity and stereoselectivity has been a great challenge in asymmetric catalysis. There is no report on the synthesis of benzo[d]isothiazole 1,1-dioxide-fused chiral eight-membered N-heterocycles thus far. Herein, we report a palladium-catalyzed asymmetric [4 + 4] cycloaddition of 3-styryl-1,2-benzoisothiazole 1,1-dioxides with γ-methylidene-δ-valerolactones at room temperature providing highly functionalized benzo[d]isothiazole 1,1-dioxide-fused chiral eight-membered N-heterocycles in high yields with excellent diastereoselectivity and enantioselectivity (76-89% yields, >20:1 dr, and 84-99% ee), in which the optimization of adjustable axially chiral cyclic phosphoramidite ligands developed by us is crucial for reactivity of the substrates and stereoselectivity of the products. Further modification of the synthesized products afforded other chiral eight-membered N-heterocycles containing a benzo[d]isothiazole 1,1-dioxide unit.
{"title":"Ligand-Promoted Palladium-Catalyzed [4 + 4] Cycloaddition Affording Benzo[d]isothiazole 1,1-Dioxide-Fused Chiral Eight-Membered N-Heterocycles.","authors":"Weixin Xiao,Zhengyi Yi,Yong Liu,Lunyu Ou,Hongyun Li,Yue Zhang,Haijun Yang,Hua Fu","doi":"10.1021/acs.orglett.5c04576","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04576","url":null,"abstract":"Synthesis of chiral eight-membered rings with high regioselectivity and stereoselectivity has been a great challenge in asymmetric catalysis. There is no report on the synthesis of benzo[d]isothiazole 1,1-dioxide-fused chiral eight-membered N-heterocycles thus far. Herein, we report a palladium-catalyzed asymmetric [4 + 4] cycloaddition of 3-styryl-1,2-benzoisothiazole 1,1-dioxides with γ-methylidene-δ-valerolactones at room temperature providing highly functionalized benzo[d]isothiazole 1,1-dioxide-fused chiral eight-membered N-heterocycles in high yields with excellent diastereoselectivity and enantioselectivity (76-89% yields, >20:1 dr, and 84-99% ee), in which the optimization of adjustable axially chiral cyclic phosphoramidite ligands developed by us is crucial for reactivity of the substrates and stereoselectivity of the products. Further modification of the synthesized products afforded other chiral eight-membered N-heterocycles containing a benzo[d]isothiazole 1,1-dioxide unit.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"35 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145711034","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04579
Ying-Zheng Ren,Nian Si,Peng-Fei Liu,Hao-Hui Xie,Wen-Chao Zhang,Peng-Fei Cui
Herein, a novel synthetic strategy for macrocycles based on a three-dimensional carborane skeleton via a cyclization reaction was developed. Further substrate scope experiments confirm that this strategy possesses excellent reaction compatibility. In addition, the cavity size of the macrocycle can be regulated by the bonding angle, in which the size of the macrocycle cavity formed by para-carborane (180°) is larger than that formed by meta-carborane (120°). More importantly, when a pyridine group is introduced into this type of macrocycle, nanotubes can be constructed through the coordination modes of [N···Ag+···N] and [N···I+···N]. The host-guest properties of the macrocycles are also explored to show the specific encapsulation of dichloromethane molecules through van der Waals forces. This work significantly enriches the structural diversity of supramolecular macrocycles and develops unique host-guest properties of the carborane-based macrocycles.
{"title":"Synthesis of Carborane-Functionalized Macrocycles: Bond-Angle-Modulated Cavities and Cation-Mediated Assembly.","authors":"Ying-Zheng Ren,Nian Si,Peng-Fei Liu,Hao-Hui Xie,Wen-Chao Zhang,Peng-Fei Cui","doi":"10.1021/acs.orglett.5c04579","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04579","url":null,"abstract":"Herein, a novel synthetic strategy for macrocycles based on a three-dimensional carborane skeleton via a cyclization reaction was developed. Further substrate scope experiments confirm that this strategy possesses excellent reaction compatibility. In addition, the cavity size of the macrocycle can be regulated by the bonding angle, in which the size of the macrocycle cavity formed by para-carborane (180°) is larger than that formed by meta-carborane (120°). More importantly, when a pyridine group is introduced into this type of macrocycle, nanotubes can be constructed through the coordination modes of [N···Ag+···N] and [N···I+···N]. The host-guest properties of the macrocycles are also explored to show the specific encapsulation of dichloromethane molecules through van der Waals forces. This work significantly enriches the structural diversity of supramolecular macrocycles and develops unique host-guest properties of the carborane-based macrocycles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"33 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145710911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04227
Zhijun Hao,Xiushan Liu,Yunfei Cai,Huifeng Yue
Herein, we present a novel iron-catalyzed regioselective C-H functionalization of silanes for the construction of oxime ethers enabled by photoinduced ligand-to-metal charge transfer (LMCT). This transformation proceeds under mild conditions using an inexpensive and commercially available iron catalyst, without the need for costly photocatalysts. The protocol features excellent site selectivity, broad substrate scope, high efficiency, and good scalability, offering a practical and economical route to organosilicon-based oxime ethers.
{"title":"Photoinduced Ligand-to-Metal Charge Transfer Enables Iron-Catalyzed Site-Selective Oxime Ether Construction at C(sp3)-H Bonds of Silanes.","authors":"Zhijun Hao,Xiushan Liu,Yunfei Cai,Huifeng Yue","doi":"10.1021/acs.orglett.5c04227","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04227","url":null,"abstract":"Herein, we present a novel iron-catalyzed regioselective C-H functionalization of silanes for the construction of oxime ethers enabled by photoinduced ligand-to-metal charge transfer (LMCT). This transformation proceeds under mild conditions using an inexpensive and commercially available iron catalyst, without the need for costly photocatalysts. The protocol features excellent site selectivity, broad substrate scope, high efficiency, and good scalability, offering a practical and economical route to organosilicon-based oxime ethers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"55 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04557
Lin Li,Lei Xiao,Zhongyu Yi,Yufen Zhao,Douglas W Stephan,Jing Guo
Converting planar arenes into C(sp3)-rich three-dimensional frameworks is an effective route to access bioisosteres of functional compounds. However, it remains challenging due to the inherent thermodynamic stability and kinetic inertness of planar arenes. In this work, we describe a simple, highly efficient, variable, and scalable method for the dearomative [2π+2σ] cycloaddition of 1-naphthols with bicyclo[1.1.0]butanes. Using this approach, 26 benzocyclohexanone-fused bicyclo[2.1.1]hexanes were obtained under mild reaction conditions in up to 99% yield with up to 19:1 dr.
{"title":"B(C6F5)3-Catalyzed Dearomative [2π+2σ] Cycloaddition of 1-Naphthols with Bicyclo[1.1.0]butanes.","authors":"Lin Li,Lei Xiao,Zhongyu Yi,Yufen Zhao,Douglas W Stephan,Jing Guo","doi":"10.1021/acs.orglett.5c04557","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04557","url":null,"abstract":"Converting planar arenes into C(sp3)-rich three-dimensional frameworks is an effective route to access bioisosteres of functional compounds. However, it remains challenging due to the inherent thermodynamic stability and kinetic inertness of planar arenes. In this work, we describe a simple, highly efficient, variable, and scalable method for the dearomative [2π+2σ] cycloaddition of 1-naphthols with bicyclo[1.1.0]butanes. Using this approach, 26 benzocyclohexanone-fused bicyclo[2.1.1]hexanes were obtained under mild reaction conditions in up to 99% yield with up to 19:1 dr.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145711036","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04290
Li Li,Shiqing Huang,Yingjian Gong,Jingpeng Han,Jianwei Liu,Guangshen Wang,Baosheng Li
The stereocontrolled construction of polycyclic architectures from linear precursors remains a significant challenge, particularly for medium-sized rings, where strain and conformational flexibility hinder efficient cyclization. Herein, we report a tandem cyclization strategy converting linear precursors to polysubstituted dihydroazepines. The resulting compounds undergo acid-promoted ring contraction to cyclopentanes with five contiguous stereocenters. Overall, this strategy provides a streamlined route to architecturally sterically congested azepine- and cyclopentane-fused dihydrofuran products with a broad substrate scope and functional group tolerance.
{"title":"Accessing Dihydroazepines and Cyclopentanes from Enynyl Ketones.","authors":"Li Li,Shiqing Huang,Yingjian Gong,Jingpeng Han,Jianwei Liu,Guangshen Wang,Baosheng Li","doi":"10.1021/acs.orglett.5c04290","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04290","url":null,"abstract":"The stereocontrolled construction of polycyclic architectures from linear precursors remains a significant challenge, particularly for medium-sized rings, where strain and conformational flexibility hinder efficient cyclization. Herein, we report a tandem cyclization strategy converting linear precursors to polysubstituted dihydroazepines. The resulting compounds undergo acid-promoted ring contraction to cyclopentanes with five contiguous stereocenters. Overall, this strategy provides a streamlined route to architecturally sterically congested azepine- and cyclopentane-fused dihydrofuran products with a broad substrate scope and functional group tolerance.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"39 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145710912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This paper describes a practical synthetic method of (hetero)aryl fused 4H-quinolizin-4-ones via (hetero)aryl sp2 C-H carbenoid functionalization of (hetero)aryl amides using pyridotriazoles with good functional group tolerance. This process demonstrates excellent site-selectivity, enabling the C-H functionalization reaction directed by an amide group by overcoming the interference of strong coordination between N-heterocycles and metal catalysis. The synthetic method represents an efficient strategy with attractive application prospects, including late-stage modification of drug molecules, total synthesis of natural products, and live-cell imaging.
{"title":"Synthesis of (Hetero)aryl Fused 4H-Quinolizin-4-ones from N-Ts Substituted (Hetero)arylamides and Pyridotriazoles.","authors":"Xin Yang,Bo Mei,Yiting Chang,Hua Tian,Heng Xu,Xiaoqiao Hong,Yi Dong","doi":"10.1021/acs.orglett.5c04190","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04190","url":null,"abstract":"This paper describes a practical synthetic method of (hetero)aryl fused 4H-quinolizin-4-ones via (hetero)aryl sp2 C-H carbenoid functionalization of (hetero)aryl amides using pyridotriazoles with good functional group tolerance. This process demonstrates excellent site-selectivity, enabling the C-H functionalization reaction directed by an amide group by overcoming the interference of strong coordination between N-heterocycles and metal catalysis. The synthetic method represents an efficient strategy with attractive application prospects, including late-stage modification of drug molecules, total synthesis of natural products, and live-cell imaging.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704572","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04279
Pauline Pfister, Daniel Čavlović, Tamara Trajkovic, Olivier Blacque, Michal Juríček
Cethrenes represent a promising platform for realizing all-organic magnetic photoswitches─provided that three requirements are met. The open form needs a thermally accessible triplet state to unlock magnetic properties, its energy relative to the closed form should lie within an accessible range, and the energy barrier between the two forms must be sufficiently high to achieve bistability. However, fulfilling the first and second criteria appear to compromise the third. Can this Catch-22 be solved? [Oxford English Dictionary defines a Catch-22 as a difficult situation or problem which cannot be resolved because the conditions necessary for its resolution are paradoxical or conflicting, with allusion to Joseph Heller’s 1961 novel of the same name.]
{"title":"Cethrene’s Catch-22: Is Trading Magnetism for Bistability Inevitable?","authors":"Pauline Pfister, Daniel Čavlović, Tamara Trajkovic, Olivier Blacque, Michal Juríček","doi":"10.1021/acs.orglett.5c04279","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04279","url":null,"abstract":"Cethrenes represent a promising platform for realizing all-organic magnetic photoswitches─provided that three requirements are met. The open form needs a thermally accessible triplet state to unlock magnetic properties, its energy relative to the closed form should lie within an accessible range, and the energy barrier between the two forms must be sufficiently high to achieve bistability. However, fulfilling the first and second criteria appear to compromise the third. Can this Catch-22 be solved? [<i>Oxford English Dictionary</i> defines a Catch-22 as a difficult situation or problem which cannot be resolved because the conditions necessary for its resolution are paradoxical or conflicting, with allusion to Joseph Heller’s 1961 novel of the same name.]","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A rigid dithienopyrrole embedded dodecaphyrin and its tris-BODIPY (bis(triisopropylsilyl-ethynyl)-substituted boron-dipyrromethene (BODIPY)) complex have been synthesized. DFT analysis showed a “ruffled” structure for dodecaphyrin and a saddle-shaped structure for tris-BODIPY. Increased conjugation of tris-BODIPY 2 showed a red-shifted absorption band (ca. 115 nm) with strong absorption in the NIR-I region as compared to its freebase analogue 1. These optical features along with nonfluorescent characteristics of 2 displayed an efficient photoacoustic imaging contrast agent.
{"title":"A Cyclic tris-BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as Photoacoustic Contrast Agent","authors":"Gayathri Krishnan, Jayaprakash Ajay, Aathira Edwin, Thondikkal Sulfikarali, Deepayan Samanta, M. Suheshkumar Singh, Sabapathi Gokulnath","doi":"10.1021/acs.orglett.5c04304","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04304","url":null,"abstract":"A rigid dithienopyrrole embedded dodecaphyrin and its <i>tris</i>-BODIPY (bis(triisopropylsilyl-ethynyl)-substituted boron-dipyrromethene (BODIPY)) complex have been synthesized. DFT analysis showed a “<i>ruffled</i>” structure for dodecaphyrin and a <i>saddle</i>-shaped structure for <i>tris</i>-BODIPY. Increased conjugation of <i>tris</i>-BODIPY <b>2</b> showed a red-shifted absorption band (ca. 115 nm) with strong absorption in the NIR-I region as compared to its freebase analogue <b>1</b>. These optical features along with nonfluorescent characteristics of <b>2</b> displayed an efficient photoacoustic imaging contrast agent.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704832","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04133
Michal Churý,Tadeáš Petrů,Radek Staník,Jan Sýkora,Václav Eigner,Pavel Lhoták
In this work, we describe a general and efficient fragment condensation method for the synthesis of monoselenacalix[4]arene as a new member of the broad calixarene family. The key fragments were obtained from the starting p-tert-butylphenol by reaction with in situ generated SeCl2 or from its formyl derivative by reaction with SeO2 in pyridine. The availability of both fragments allowed us to test two different independent macrocyclization routes, leading to the final selenacalixarene in good yields. The first successful attempts to immobilize the new system were made, and the basic dynamics of the macrocycles in solution were studied using VT NMR techniques. The selenium analogue of calix[4]arene was successfully immobilized in the cone conformation, suggesting its potential use in supramolecular chemistry.
{"title":"Newcomer to the Calixarene Family: Synthesis and Characterization of Selenacalix[4]arene.","authors":"Michal Churý,Tadeáš Petrů,Radek Staník,Jan Sýkora,Václav Eigner,Pavel Lhoták","doi":"10.1021/acs.orglett.5c04133","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04133","url":null,"abstract":"In this work, we describe a general and efficient fragment condensation method for the synthesis of monoselenacalix[4]arene as a new member of the broad calixarene family. The key fragments were obtained from the starting p-tert-butylphenol by reaction with in situ generated SeCl2 or from its formyl derivative by reaction with SeO2 in pyridine. The availability of both fragments allowed us to test two different independent macrocyclization routes, leading to the final selenacalixarene in good yields. The first successful attempts to immobilize the new system were made, and the basic dynamics of the macrocycles in solution were studied using VT NMR techniques. The selenium analogue of calix[4]arene was successfully immobilized in the cone conformation, suggesting its potential use in supramolecular chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"110 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-09DOI: 10.1021/acs.orglett.5c04699
Zhenhong Gan,Xiaoyan Cai,Liming Chen,Lele Zhang,Jiaxin Lin,Mingqiang Huang,Lina Cai,Shunyou Cai
Lanthanum-catalyzed tandem C(sp3)-H oxidation/spirocyclization under ambient conditions using molecular oxygen is reported. This method exhibits broad functional group tolerance and enables precise functionalization of complex scaffolds. The reaction proceeds via a light-absorbing lanthanum complex assembled through in situ multicomponent coordination, operating through synergistic intramolecular energy transfer and single-electron transfer pathways. This approach provides efficient access to diverse N,O- and O,O-spirocyclic compounds. Mechanistic studies establish that lanthanum bromide acts not only as the photosensitizer metal center, generating bromine radicals for C-H cleavage, but also as a Lewis acid catalyst promoting cyclization and spirocyclization.
{"title":"Photoinduced Lanthanum Catalysis: C-H Activation and Spirocyclization.","authors":"Zhenhong Gan,Xiaoyan Cai,Liming Chen,Lele Zhang,Jiaxin Lin,Mingqiang Huang,Lina Cai,Shunyou Cai","doi":"10.1021/acs.orglett.5c04699","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c04699","url":null,"abstract":"Lanthanum-catalyzed tandem C(sp3)-H oxidation/spirocyclization under ambient conditions using molecular oxygen is reported. This method exhibits broad functional group tolerance and enables precise functionalization of complex scaffolds. The reaction proceeds via a light-absorbing lanthanum complex assembled through in situ multicomponent coordination, operating through synergistic intramolecular energy transfer and single-electron transfer pathways. This approach provides efficient access to diverse N,O- and O,O-spirocyclic compounds. Mechanistic studies establish that lanthanum bromide acts not only as the photosensitizer metal center, generating bromine radicals for C-H cleavage, but also as a Lewis acid catalyst promoting cyclization and spirocyclization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"140 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704575","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}