{"title":"Collaborative Reduction-Induced Nickel-Catalytic Selective C–S Coupling of Aryl Di/Trithiosulfonates with Aryl Halides","authors":"Lulu Liu, Jiaqi Hou, Yingying Ma, Wen-Hua Xu, Ji-Quan Liu, Dianhu Zhu","doi":"10.1021/acs.orglett.4c04390","DOIUrl":null,"url":null,"abstract":"Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes of multiple S–S bonds. The utilization of aryl di- and trithiosulfonates in nickel-catalyzed reductive coupling with aryl halides has been unexplored. Herein, we unprecedentedly describe PPh<sub>3</sub> and Zn-collaborative reduction-induced nickel-catalytic selective C–S coupling of aryl di/trithiosulfonates with aryl halides to access sulfides over common disulfides or trisulfides. Diverse mechanistic studies indicate that the key design of such a reaction could be attributed to the employment of PPh<sub>3</sub> and MgCl<sub>2</sub>, which collaborate with Zn for the improved reduction potential that enables selective reductive cleavage of PhSO<sub>2</sub>(S)<sub><i>n</i></sub>aryl (<i>n</i> = 2, 3) to electrophilic sulfur species for reductive sulfuration in a controllable fashion.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04390","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes of multiple S–S bonds. The utilization of aryl di- and trithiosulfonates in nickel-catalyzed reductive coupling with aryl halides has been unexplored. Herein, we unprecedentedly describe PPh3 and Zn-collaborative reduction-induced nickel-catalytic selective C–S coupling of aryl di/trithiosulfonates with aryl halides to access sulfides over common disulfides or trisulfides. Diverse mechanistic studies indicate that the key design of such a reaction could be attributed to the employment of PPh3 and MgCl2, which collaborate with Zn for the improved reduction potential that enables selective reductive cleavage of PhSO2(S)naryl (n = 2, 3) to electrophilic sulfur species for reductive sulfuration in a controllable fashion.
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.
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