Radical Reactions

Chapter 13 Radical Reactions A. F. Parsons, A. F. Parsons Department of Chemistry, University of York, Heslington, York, UKSearch for more papers by this authorT. F. Parsons, T. F. Parsons Wyke Sixth Form College, Hull, UKSearch for more papers by this author A. F. Parsons, A. F. Parsons Department of Chemistry, University of York, Heslington, York, UKSearch for more papers by this authorT. F. Parsons, T. F. Parsons Wyke Sixth Form College, Hull, UKSearch for more papers by this author Book Editor(s):Mark Moloney, Mark Moloney University of Oxford, Mansfield Road, Oxford, UK, OX1 3TA United KingdomSearch for more papers by this author First published: 15 March 2024 https://doi.org/10.1002/9781119716846.ch13Book Series:Organic Reaction Mechanisms Series AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary A review of photocatalytic strategies, involving radical intermediates of importance in organic synthesis, has appeared. The fact that photocatalytic cycles are composed of three steps, namely excitation, quenching, and finally restoration, is highlighted. The review has a particular emphasis on the restoration step, exploring how the deactivated form of the catalyst is converted back into the original state, which permits the cycle to start over again. It classifies photocatalytic processes according to what species is responsible for the restoration step, such as the substrate, an intermediate, or a sacrificial agent. The stereoselective bromoboration of acetylene with boron tribromide is investigated. The mechanism was studied by experiments and calculations, and besides the syn-addition mechanism (proceeding via a four-membered transition state) a radical and polar anti-addition mechanism was postulated. References Capaldo , L. , and Ravelli , D. , Eur. J. Org. Chem. , 2020 , 2783 (2020). 10.1002/ejoc.202000144 Google Scholar Lee , Y. and Kwon , M. S. , Eur. J. Org. Chem. , 2020 , 6028 (2020). 10.1002/ejoc.202000720 Google Scholar Yuan , Y. Q. , Majumder , S. , Yang , M. H. , and Guo , S. R. , Tetrahedron Lett. , 61 , 15106 ( 2020 ). Google Scholar Tang , H. T. , Jia , J. S. , and Pan , Y. M. , Org. Biomol. Chem. , 18 , 5315 ( 2020 ). 10.1039/D0OB01008A CASPubMedWeb of Science®Google Scholar Bartos , P. , Young , V. 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