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 Okt. 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

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