Issue 8, 2022

Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Abstract

10 mol% B(2,6-C6F2H3)3 in the presence of excess tetramethylpiperidine (TMP) and H2 (or D2) is shown to catalyze the hydrogenative dehalogenation of benzyl-halides to give corresponding toluene derivatives. These reactions proceed via an initial FLP activation of H2 yielding the ammonium hydridoborate [TMPH][HB(2,6-C6F2H3)3]. This species acts in analogy to a FLP to cooperatively activate C–X bond (X = Cl, Br, I) of benzyl-halides delivering hydride and generating the corresponding ammonium halide salts.

Graphical abstract: Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Supplementary files

Article information

Article type
Communication
Submitted
21 Oct 2021
Accepted
20 Dec 2021
First published
20 Dec 2021

Chem. Commun., 2022,58, 1175-1178

Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

T. Wang, M. Xu, A. R. Jupp, S. Chen, Z. Qu, S. Grimme and D. W. Stephan, Chem. Commun., 2022, 58, 1175 DOI: 10.1039/D1CC05943B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements