{"title":"Reaction of Carboranyl Lithium and 2,3-Dichloroquinoxaline to Synthesize Carborane-Fused N-Heteroaromatic","authors":"Ying Li, Peng Zhao, Caixia Jia, Nianhe Sun, Yan-Na Ma* and Zheng Duan*, ","doi":"10.1021/acs.organomet.3c00516","DOIUrl":null,"url":null,"abstract":"<p >Nucleophilic substitution of B–H is an important strategy for the synthesis of carborane derivatives. Although the intermolecular B–H nucleophilic substitution has been widely explored, intramolecular B–H nucleophilic substitution has rarely been reported. Herein, we synthesized a novel carborane-fused <i>N</i>-heteroaromatic through a transition-metal-free reaction between carboranyl lithium and 2,3-dichloroquinoxaline. Two intermolecular C–Cl nucleophilic substitutions and one intramolecular B–H nucleophilic substitution with carboranyl lithium were involved in this transformation. Instead of the most electron-deficient B(3)–H vertex, the B–H nucleophilic substitution selectively occurred on the B(4)–H vertex. This method provides a new method for the synthesis of carborane-fused ring compounds.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":null,"pages":null},"PeriodicalIF":2.5000,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organometallics","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.organomet.3c00516","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
Nucleophilic substitution of B–H is an important strategy for the synthesis of carborane derivatives. Although the intermolecular B–H nucleophilic substitution has been widely explored, intramolecular B–H nucleophilic substitution has rarely been reported. Herein, we synthesized a novel carborane-fused N-heteroaromatic through a transition-metal-free reaction between carboranyl lithium and 2,3-dichloroquinoxaline. Two intermolecular C–Cl nucleophilic substitutions and one intramolecular B–H nucleophilic substitution with carboranyl lithium were involved in this transformation. Instead of the most electron-deficient B(3)–H vertex, the B–H nucleophilic substitution selectively occurred on the B(4)–H vertex. This method provides a new method for the synthesis of carborane-fused ring compounds.
期刊介绍:
Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.