Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Tontong Wang; Maotong Xu; Andrew Jupp; Shi-Ming Chen; Zheng-Wang Qu; Stefan Grimme; Douglas Stephan

doi:10.1039/D1CC05943B

Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Tontong Wang, Maotong Xu, Andrew Jupp, Shi-Ming Chen, Zheng-Wang Qu, Stefan Grimme, Douglas Stephan

Chemistry

Research output: Contribution to journal › Article › peer-review

59 Downloads (Pure)

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.

Original language	English
Pages (from-to)	1175-1178
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	8
Early online date	20 Dec 2021
DOIs	https://doi.org/10.1039/D1CC05943B
Publication status	Published - 22 Jan 2022

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/D1CC05943BLicence: None: All rights reserved

WangT2021FrustratedAccepted author manuscript, 313 KBLicence: None: All rights reserved

Cite this

@article{1c3564ef67ed43cda37d06fb227e64c6,

title = "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.",

author = "Tontong Wang and Maotong Xu and Andrew Jupp and Shi-Ming Chen and Zheng-Wang Qu and Stefan Grimme and Douglas Stephan",

year = "2022",

month = jan,

day = "22",

doi = "10.1039/D1CC05943B",

language = "English",

volume = "58",

pages = "1175--1178",

journal = "Chemical Communications ",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "8",

}

TY - JOUR

T1 - Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

AU - Wang, Tontong

AU - Xu, Maotong

AU - Jupp, Andrew

AU - Chen, Shi-Ming

AU - Qu, Zheng-Wang

AU - Grimme, Stefan

AU - Stephan, Douglas

PY - 2022/1/22

Y1 - 2022/1/22

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85123782475&partnerID=8YFLogxK

U2 - 10.1039/D1CC05943B

DO - 10.1039/D1CC05943B

M3 - Article

SN - 1359-7345

VL - 58

SP - 1175

EP - 1178

JO - Chemical Communications

JF - Chemical Communications

IS - 8

ER -

Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this