Indene formation upon borane-induced cyclization of arylallenes, 1, 1-carboboration, and retro-hydroboration. Issue 45 (6th May 2021)

• Record Type: Journal Article
• Authors: Hasenbeck, Max; Wech, Felix; Averdunk, Arthur; Becker, Jonathan; Gellrich, Urs
• Is Part Of: Chemical communications. Volume 57:Issue 45(2021)
• Page Start: 5518
• Page End: 5521
• Publication Date: 2021-05-06
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc01750k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The formation of pentafluorophenyl indenes upon reaction of arylallenes with B(C6 F5 )3 is reported. Key steps are a 1, 1-carboboration and a retrohydroboration. Abstract : We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1, 1- carboboration to be the C–C bond-forming step.