Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny*, Heather D. Maynard* and K. N. Houk*,
{"title":"Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry","authors":"Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny*, Heather D. Maynard* and K. N. Houk*, ","doi":"10.1021/acs.orglett.4c0404510.1021/acs.orglett.4c04045","DOIUrl":null,"url":null,"abstract":"<p >Oxidant-free Au(I)/Au(III)-catalyzed cross-coupling has been recently enabled by the use of bidentate <i>P</i>,<i>N</i>-ligands. To further develop these <i>P</i>,<i>N</i>-ligands, computational studies were performed to understand their effects on the oxidative addition of aryl iodide electrophiles with Au(I). Using this mechanistic understanding, six new electron-rich <i>P</i>,<i>N</i>-ligands were synthesized. The ligand exchange equilibrium and reductive elimination were then characterized by using a Au(III)-mediated <i>S</i>-arylation reaction. The results detailed herein provide new fundamental insights in Au(I)/Au(III) ligand design.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10875–10879 10875–10879"},"PeriodicalIF":4.9000,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.4c04045","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.4c04045","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
Oxidant-free Au(I)/Au(III)-catalyzed cross-coupling has been recently enabled by the use of bidentate P,N-ligands. To further develop these P,N-ligands, computational studies were performed to understand their effects on the oxidative addition of aryl iodide electrophiles with Au(I). Using this mechanistic understanding, six new electron-rich P,N-ligands were synthesized. The ligand exchange equilibrium and reductive elimination were then characterized by using a Au(III)-mediated S-arylation reaction. The results detailed herein provide new fundamental insights in Au(I)/Au(III) ligand design.
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.