Issue 45, 2021

Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

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.

Graphical abstract: Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

Supplementary files

Article information

Article type
Communication
Submitted
02 Apr 2021
Accepted
29 Apr 2021
First published
29 Apr 2021

Chem. Commun., 2021,57, 5518-5521

Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

M. Hasenbeck, F. Wech, A. Averdunk, J. Becker and U. Gellrich, Chem. Commun., 2021, 57, 5518 DOI: 10.1039/D1CC01750K

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