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Iron-Catalyzed Borylation of Aryl Trifluoromethoxides 铁催化芳基三氟甲氧化物的硼化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-23 DOI: 10.1021/acs.orglett.5c01712
Jongheon Jeong, Jun Hee Lee, Eunsung Lee
{"title":"Iron-Catalyzed Borylation of Aryl Trifluoromethoxides","authors":"Jongheon Jeong, Jun Hee Lee, Eunsung Lee","doi":"10.1021/acs.orglett.5c01712","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01712","url":null,"abstract":"The trifluoromethoxy group, a bioisostere of the methoxy group, has emerged as a key functional group in agrochemicals and pharmaceuticals due to its high stability and lipophilicity. While extensive research exists on C(sp<sup>2</sup>)–OCF<sub>3</sub> bond formation, strategies for activating these bonds remain underexplored. Here, we report a highly chemoselective iron-catalyzed borylation of aryl trifluoromethoxides using a commercially available iron salt and an inexpensive ligand. Mechanistic investigations suggest a heterogeneous catalytic pathway without the formation of Grignard intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 42 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122595","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}
引用次数: 0
Design of Fast Redox-Controlled Self-Immolative Selenium-Based Cysteine Surrogates. 快速氧化还原控制自焚硒基半胱氨酸替代物的设计。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-23 DOI: 10.1021/acs.orglett.5c01514
Eliott Roy,Vincent Diemer,Oleg Melnyk
{"title":"Design of Fast Redox-Controlled Self-Immolative Selenium-Based Cysteine Surrogates.","authors":"Eliott Roy,Vincent Diemer,Oleg Melnyk","doi":"10.1021/acs.orglett.5c01514","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01514","url":null,"abstract":"The self-immolation of N-selenoethyl cysteine derivatives into cysteine exhibits a strong Thorpe-Ingold effect. Notably, the gem-dimethyl substitution α to the selenium atom achieved rate accelerations up to 252-fold, enabling Cys unmasking through C-N bond cleavage within minutes. These investigations offer valuable insights into the mechanism of selenoethyl arm breakdown and new redox-sensitive Cys surrogates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122321","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}
引用次数: 0
Synthesis of 3,4-Fused Pyrroles with Seven-Membered Carbocycles via Cascade C–C σ-Bond Cleavage/Intramolecular Cyclization Reactions 级联C-C σ键裂解/分子内环化反应合成7元碳环3,4-熔融吡咯
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-23 DOI: 10.1021/acs.orglett.5c01607
Yan Wang, Qiongwen Kang, Nana Fei, Peng He, Zongkang Wang, Lingkai Kong, Yanzhong Li
{"title":"Synthesis of 3,4-Fused Pyrroles with Seven-Membered Carbocycles via Cascade C–C σ-Bond Cleavage/Intramolecular Cyclization Reactions","authors":"Yan Wang, Qiongwen Kang, Nana Fei, Peng He, Zongkang Wang, Lingkai Kong, Yanzhong Li","doi":"10.1021/acs.orglett.5c01607","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01607","url":null,"abstract":"A novel tandem reaction involving amino-substituted ynones and cyclic carbonyls has been developed, efficiently synthesizing 3,4-fused pyrroles with seven-membered carbocycles by a one-pot method. This reaction proceeds through a cascade ring-expansion of cyclic carbonyls, followed by intramolecular cyclization reactions. This metal-free strategy enables the concurrent construction of the medium-sized ring and the pyrrole ring, exhibiting a high step economy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122594","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}
引用次数: 0
Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins 维生素B12和胶束溶液使环氧化合物和叠氮醚与亲电烯烃的区域选择性开环
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-23 DOI: 10.1021/acs.orglett.5c01376
Kitti Franciska Szabó, Tomasz Wdowik, Aleksandra Krzeszewska, Krzysztof Mazurek, Martin P. Andersson, Dorota Gryko
{"title":"Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins","authors":"Kitti Franciska Szabó, Tomasz Wdowik, Aleksandra Krzeszewska, Krzysztof Mazurek, Martin P. Andersson, Dorota Gryko","doi":"10.1021/acs.orglett.5c01376","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01376","url":null,"abstract":"Vitamin B<sub>12</sub>, a water-soluble cobalt complex, is inherently predisposed to catalyze reactions under aqueous conditions. Despite its potential, adopting this strategy for transformations of hydrophobic reagents has been challenging, because of their low aqueous solubility. Here, we demonstrate that vitamin B<sub>12</sub> promotes the reaction of epoxides and aziridines with electrophilic olefins in a micellar system. The desired products are obtained efficiently in a fully regioselective manner. This green catalytic approach further advances the use of vitamin B<sub>12</sub> in sustainable catalysis providing a valuable method to synthesize important intermediates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"45 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122598","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}
引用次数: 0
Alkynyl Sulfide: An Unexplored yet Versatile Alkynyl Species for Chemoselective Cross-Electrophile Coupling. 炔基硫化物：一种用于化学选择性交叉亲电偶联的未开发的多功能炔基物种。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-23 DOI: 10.1021/acs.orglett.5c01547
Donghui Xing,Jinlin Liu,Liangbin Huang
{"title":"Alkynyl Sulfide: An Unexplored yet Versatile Alkynyl Species for Chemoselective Cross-Electrophile Coupling.","authors":"Donghui Xing,Jinlin Liu,Liangbin Huang","doi":"10.1021/acs.orglett.5c01547","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01547","url":null,"abstract":"The development of robust and readily available carbon electrophiles for cross-electrophile coupling (XEC) is important and highly desirable. Herein, we report a cobalt-catalyzed highly chemoselective XEC between alkynyl sulfides and various alkyl halides, which tolerates otherwise widely employed coupling handles such as a series of aromatic (pseudo)halogens (Ar-I/Br/Cl/OTf/OTs/SMe) and provides an easy and efficient method for synthesizing internal alkynes (>60 examples achieving up to 96% yields). Mechanistic studies have revealed that the leaving sulfide anion of alkynyl sulfides adjusts the reactivity of alkynyl-Co intermediates, enabling excellent chemoselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"57 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122318","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}
引用次数: 0
Enantioselective Total Synthesis of (-)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2'-indoline Structure. 不对称氢化和Aza-Wacker环化对映选择性全合成(-)-缬沙脒构建核心螺旋环戊烷-1,2'-吲哚啉结构
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-22 DOI: 10.1021/acs.orglett.5c01615
Fan Yang,Xia-Lin Wang,Feng-Kai Zhao,Huai-Yu Bin,Jian-Hua Xie
{"title":"Enantioselective Total Synthesis of (-)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2'-indoline Structure.","authors":"Fan Yang,Xia-Lin Wang,Feng-Kai Zhao,Huai-Yu Bin,Jian-Hua Xie","doi":"10.1021/acs.orglett.5c01615","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01615","url":null,"abstract":"An enantioselective total synthesis of (-)-vallesamidine is described, integrating asymmetric hydrogenation with aza-Wacker cyclization to form the chiral spirocyclopentane-1,2'-indoline. Intramolecular Stetter reaction and alkylation are employed to construct a tetracyclic framework featuring a chiral quaternary carbon center. Schmidt rearrangement and intramolecular aldol condensation facilitate the formation of the D and E rings. This synthesis achieves (-)-vallesamidine in 14 steps in an overall yield of 4.2% from an exocyclic enone ester.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"31 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144114239","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}
引用次数: 0
C3-H Trifluoroacetylation of Quinolines and Pyridines: Access to Heteroaryl Ketones, Carboxylic Acids, and Amides. 喹啉和吡啶的C3-H三氟乙酰化：获得杂芳基酮、羧酸和酰胺。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-22 DOI: 10.1021/acs.orglett.5c01350
Xu Wang,An Yan,Hua Xiao,Weiwei Xiao,Liqing Xu,Dong Wang
{"title":"C3-H Trifluoroacetylation of Quinolines and Pyridines: Access to Heteroaryl Ketones, Carboxylic Acids, and Amides.","authors":"Xu Wang,An Yan,Hua Xiao,Weiwei Xiao,Liqing Xu,Dong Wang","doi":"10.1021/acs.orglett.5c01350","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01350","url":null,"abstract":"Despite extensive synthetic endeavors, achieving direct C3-H trifluoroacetylation in quinolines/pyridines continues to pose significant challenges. We report a protocol for direct C3-H trifluoroacetylation of quinolines and pyridines under transition-metal-free conditions. Readily accessible quinolines or pyridines serve as starting materials and undergo a dearomatization process to generate dihydroquinoline or dihydropyridine intermediates, which readily react with trifluoracetic anhydride. Subsequent acid-promoted dealkylative rearomatization delivers heteroaryl trifluoromethyl ketones. This tandem process is accomplished in a two-pot, one column process. The trifluoroacetyl group in the resulting heteroarenes can be readily transformed into a variety of functional groups.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"44 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144114247","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}
引用次数: 0
Pd-Catalyzed Regioselective Homobenzannulation of Enynals 钯催化环氧乙烷的区域选择性均苯环制
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-22 DOI: 10.1021/acs.orglett.5c01348
Jianwei Liu, Xiaolan Xin, Yongjian Yang, Xiaoya Sun, Xingcan Zhang, Jingpeng Han, Baosheng Li
{"title":"Pd-Catalyzed Regioselective Homobenzannulation of Enynals","authors":"Jianwei Liu, Xiaolan Xin, Yongjian Yang, Xiaoya Sun, Xingcan Zhang, Jingpeng Han, Baosheng Li","doi":"10.1021/acs.orglett.5c01348","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01348","url":null,"abstract":"Regio- and chemoselectivities in the synthesis of polysubstituted benzenes have posed a significant scientific obstacle for an extended period. Herein, we report a tunable Pd-catalyzed homobenzannulation of enynals, enabling divergent construction of 1,2,4-tri- and 1,4-disubstituted benzenes from identical substrates via unconventional selectivity. In particular, the interesting reaction model is verified by a variety of control experiments, offering theoretically valuable insight for the rational design of benzannulation reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122596","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}
引用次数: 0
TEMPO-Mediated Polyyne Cyclization tempo介导的聚乙烯环化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-22 DOI: 10.1021/acs.orglett.5c00651
Qiaofeng Liang, Ying Xia, Chenlong Zhu, Bingfeng Sun
{"title":"TEMPO-Mediated Polyyne Cyclization","authors":"Qiaofeng Liang, Ying Xia, Chenlong Zhu, Bingfeng Sun","doi":"10.1021/acs.orglett.5c00651","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00651","url":null,"abstract":"In this work, we report the cyclization of sulfur-linked tetraynes under 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) radical conditions, leading to the formation of novel pentadehydro-Diels–Alder-type addition products. Through this study, we expand the scope of radical-mediated cyclization reactions of polyyne compounds. The results offer new opportunities for the development of radical-based synthetic methodologies.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"41 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122678","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}
引用次数: 0
Energy-Transfer-Enabled 1,4-Amino Migration and C–O Diradical Recombination for Norrish–Yang-Type Epoxidation norrish - yang型环氧化反应的能量转移使1,4-氨基迁移和C-O双自由基重组
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-22 DOI: 10.1021/acs.orglett.5c01450
Dan-Na Chen, Lu-Lu Qin, Di-Jing Luo, Yu Lv, Hong-Yu Yang, Dan-Dan Ye, Peng-Ju Xia
{"title":"Energy-Transfer-Enabled 1,4-Amino Migration and C–O Diradical Recombination for Norrish–Yang-Type Epoxidation","authors":"Dan-Na Chen, Lu-Lu Qin, Di-Jing Luo, Yu Lv, Hong-Yu Yang, Dan-Dan Ye, Peng-Ju Xia","doi":"10.1021/acs.orglett.5c01450","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01450","url":null,"abstract":"An energy-transfer-enabled photochemical strategy merges 1,4-nitrogen migration with Norrish–Yang-type epoxidation to achieve skeletal editing of molecular frameworks. This approach bypasses classical di-π-methane rearrangements, providing an oxidant-free and atom-economical route to epoxides via controlled C–O diradical recombination. The protocol accommodates &gt;40 diverse substrates, including arenes, heterocycles, and bioactive motifs, enabling late-stage functionalization of complex architectures. Scalability is demonstrated through gram-scale synthesis (84% yield) and one-pot cascades. Mechanistic studies reveal a triplet energy-transfer pathway distinct from radical chain processes, with nitrogen migration directing regioselective diradical recombination.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144114424","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}
引用次数: 0
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