Ruihong Wang, Xiaoxia Han, Jin Zhang*, Nana Chen, Li Sun, Gaopeng Zhang and Michal Szostak*,
{"title":"结构灵活的(噻唑-2-基)Pd(烯丙基)Cl配合物用于芳基卤化物和酰胺的Suzuki-Miyaura交叉偶联。","authors":"Ruihong Wang, Xiaoxia Han, Jin Zhang*, Nana Chen, Li Sun, Gaopeng Zhang and Michal Szostak*, ","doi":"10.1021/acs.orglett.5c03118","DOIUrl":null,"url":null,"abstract":"<p >This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)–NHC catalysts demonstrate superior reactivity in chemoselective Suzuki–Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 36","pages":"10054–10059"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides\",\"authors\":\"Ruihong Wang, Xiaoxia Han, Jin Zhang*, Nana Chen, Li Sun, Gaopeng Zhang and Michal Szostak*, \",\"doi\":\"10.1021/acs.orglett.5c03118\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)–NHC catalysts demonstrate superior reactivity in chemoselective Suzuki–Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 36\",\"pages\":\"10054–10059\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03118\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03118","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides
This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)–NHC catalysts demonstrate superior reactivity in chemoselective Suzuki–Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.