Facile protocol for water-tolerant “frustrated Lewis pair”-catalyzed hydrogenation

Daniel J. Scott; Trevor R. Simmons; Elliot J. Lawrence; Gregory G. Wildgoose; Matthew J. Fuchter; Andrew E. Ashley

doi:10.1021/acscatal.5b01417

Facile protocol for water-tolerant “frustrated Lewis pair”-catalyzed hydrogenation

Daniel J. Scott, Trevor R. Simmons, Elliot J. Lawrence, Gregory G. Wildgoose, Matthew J. Fuchter, Andrew E. Ashley

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

107 Citations (SciVal)

34 Downloads (Pure)

Abstract

Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensitivity of FLPs, 1,4-dioxane solutions of B(C6F5)3 actually show appreciable moisture tolerance and can catalyze hydrogenation of a range of weakly basic substrates without the need for rigorously inert conditions. In particular, reactions can be performed directly in commercially available nonanhydrous solvents without subsequent drying or use of internal desiccants.

Original language	English
Pages (from-to)	5540-5544
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.5b01417
Publication status	Published - 17 Aug 2015

Keywords

“frustrated Lewis pairs”
catalytic hydrogenation
water tolerance
solvent effects
metal-free

Access to Document

10.1021/acscatal.5b01417

ACS_Catalysis_Scott_etal_2015_5_9_5540
This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
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(PiHOMER) Pioneering Heterogeneous Organometallic-Mediated Electrocatalytic Reactions
Wildgoose, G. & Blagg, R.
CEC (Framework 7)
1/08/12 → 31/07/17
Project: Research

107 Citations (Scopus)
2 Article

Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: Towards the combined electrochemical-frustrated Lewis pair activation of H₂
Blagg, R. J., Lawrence, E. J., Resner, K., Oganesyan, V. S., Herrington, T. J., Ashley, A. E. & Wildgoose, G. G., 14 Apr 2016, In: Dalton Transactions. 45, 14, p. 6023-6031 9 p.
Research output: Contribution to journal › Article › peer-review

Open Access
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28 Citations (Scopus)

9 Downloads (Pure)
A combined "electrochemical-frustrated Lewis pair" approach to hydrogen activation: surface catalytic effects at platinum electrodes
Lawrence, E. J., Blagg, R. J., Hughes, D. L., Ashley, A. E. & Wildgoose, G. G., 7 Jan 2015, In: Chemistry - A European Journal. 21, 2, p. 900-906 7 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File

15 Citations (Scopus)

17 Downloads (Pure)

Cite this

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title = "Facile protocol for water-tolerant “frustrated Lewis pair”-catalyzed hydrogenation",

abstract = "Despite rapid advances in the field of metal-free, “frustrated Lewis pair” (FLP)-catalyzed hydrogenation, the need for strictly anhydrous reaction conditions has hampered wide-scale uptake of this methodology. Herein, we report that, despite the generally perceived moisture sensitivity of FLPs, 1,4-dioxane solutions of B(C6F5)3 actually show appreciable moisture tolerance and can catalyze hydrogenation of a range of weakly basic substrates without the need for rigorously inert conditions. In particular, reactions can be performed directly in commercially available nonanhydrous solvents without subsequent drying or use of internal desiccants.",

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Facile protocol for water-tolerant “frustrated Lewis pair”-catalyzed hydrogenation

Abstract

Keywords

Access to Document

Projects

(PiHOMER) Pioneering Heterogeneous Organometallic-Mediated Electrocatalytic Reactions

Research output

Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: Towards the combined electrochemical-frustrated Lewis pair activation of H2

A combined "electrochemical-frustrated Lewis pair" approach to hydrogen activation: surface catalytic effects at platinum electrodes

Cite this

Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: Towards the combined electrochemical-frustrated Lewis pair activation of H₂