Pedro H. R. Oliveira, Marieli O. Rodrigues, Caren D. G. da Silva, Josina Bohlen, Merle Arrowsmith, Arumugam Jayaraman, Lukas Lubczyk, Felipe Fantuzzi, Eufrânio N. da Silva Júnior, Holger Braunschweig
{"title":"Straightforward Formation of Borirenes from Boroles and Dialkynes","authors":"Pedro H. R. Oliveira, Marieli O. Rodrigues, Caren D. G. da Silva, Josina Bohlen, Merle Arrowsmith, Arumugam Jayaraman, Lukas Lubczyk, Felipe Fantuzzi, Eufrânio N. da Silva Júnior, Holger Braunschweig","doi":"10.1002/anie.202423391","DOIUrl":null,"url":null,"abstract":"We report a selective one‐step synthesis of perarylated borirenes by reaction of antiaromatic boroles with 1,4‐diarylbuta‐1,3‐diynes. Mechanistic studies, both experimental and computational, reveal key intermediates, including boranorbornadiene and 7‐borabicyclo[4.1.0]heptadiene species, which are all in equilibrium with each other, ultimately leading to borirene formation by migration of the boranediyl bridge from the cyclohexadiene ring to the remaining exocyclic alkyne residue.","PeriodicalId":125,"journal":{"name":"Angewandte Chemie International Edition","volume":"29 1","pages":""},"PeriodicalIF":16.1000,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie International Edition","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/anie.202423391","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
We report a selective one‐step synthesis of perarylated borirenes by reaction of antiaromatic boroles with 1,4‐diarylbuta‐1,3‐diynes. Mechanistic studies, both experimental and computational, reveal key intermediates, including boranorbornadiene and 7‐borabicyclo[4.1.0]heptadiene species, which are all in equilibrium with each other, ultimately leading to borirene formation by migration of the boranediyl bridge from the cyclohexadiene ring to the remaining exocyclic alkyne residue.
期刊介绍:
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.