{"title":"Design Principles for Activating Organohalides with Hydrogen-Derived Electrons","authors":"Kaho Yamada, Yuu Kajiwara, Takeshi Yatabe, Ki-Seok Yoon, Hidetaka Nakai and Seiji Ogo*, ","doi":"10.1021/acs.organomet.4c0036010.1021/acs.organomet.4c00360","DOIUrl":null,"url":null,"abstract":"<p >Replacing wasteful metal-based reducing agents with H<sub>2</sub> is an important goal for green chemistry. For this reason, we outline our design principles for building catalysts that use electrons from hydrogen to activate organohalides for reaction. These designs rely on an electron-withdrawing ligand to support low-valent metal centers, an electron-donating ligand to support oxidative addition, and the capacity for vacant sites to allow substrate docking. We begin by outlining our previous work in this field before describing a new rhodium complex that activates a particularly stubborn organohalide, 2,2-dibromopropane, using electrons from hydrogen. We then react this activated organohalide with styrene to generate a synthetically useful fragment of murraol in an efficient manner.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"43 22","pages":"2916–2925 2916–2925"},"PeriodicalIF":2.5000,"publicationDate":"2024-11-05","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.4c00360","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
Replacing wasteful metal-based reducing agents with H2 is an important goal for green chemistry. For this reason, we outline our design principles for building catalysts that use electrons from hydrogen to activate organohalides for reaction. These designs rely on an electron-withdrawing ligand to support low-valent metal centers, an electron-donating ligand to support oxidative addition, and the capacity for vacant sites to allow substrate docking. We begin by outlining our previous work in this field before describing a new rhodium complex that activates a particularly stubborn organohalide, 2,2-dibromopropane, using electrons from hydrogen. We then react this activated organohalide with styrene to generate a synthetically useful fragment of murraol in an efficient manner.
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.
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