Journal article
Influence of Lewis acid strength on hydride transfer to unsaturated substrates
Dalton transactions : an international journal of inorganic chemistry, Vol.47(11), pp.3985-3991
02/21/2018
Handle:
https://hdl.handle.net/2376/113529
PMID: 29464246
Abstract
Hydride transfer promoted by the coordination of a substrate molecule to a Lewis acid is a critical step in many catalytic transformations. This computational study investigates the nature of the interaction between a polar substrate molecule and a Lewis acid by examining the influence of Lewis acid strength on the ability to reduce (transfer a hydride to) the coordinated substrate molecule. To investigate this interaction, the coordination of 10 probe substrates to seven Lewis acids was analyzed. Coordination of the probe substrate molecules to a Lewis acid resulted in a more favorable reduction of the substrate molecule by 20-70 kcal mol
. Further examination of the coordination of the substrate molecules to Lewis acids of varying Lewis acid strengths resulted in a direct linear correlation between the ability of the Lewis acid-substrate adduct to accept a hydride and the Lewis acid strength. The linear correlations also revealed that between 44 and 70% of the Lewis acidity of the Lewis acids translated to the Lewis acid-substrate adducts. From the results obtained in this study, the minimum Lewis acid strength needed to activate the substrates for the reduction with [BH
]
and the implications of employing a Lewis acid to promote the reduction of an unsaturated polar substrate in catalytic reactions are also described.
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Details
- Title
- Influence of Lewis acid strength on hydride transfer to unsaturated substrates
- Creators
- Ian A Kieffer - Department of Chemistry, Washington State University, Pullman, WA 99164, USA. zachariah.heiden@wsu.eduNicholas R Treich - Department of Chemistry, Washington State University, Pullman, WA 99164, USA. zachariah.heiden@wsu.eduJordan L Fernandez - Department of Chemistry, Washington State University, Pullman, WA 99164, USA. zachariah.heiden@wsu.eduZachariah M Heiden - Department of Chemistry, Washington State University, Pullman, WA 99164, USA. zachariah.heiden@wsu.edu
- Publication Details
- Dalton transactions : an international journal of inorganic chemistry, Vol.47(11), pp.3985-3991
- Academic Unit
- Chemistry, Department of
- Publisher
- England
- Identifiers
- 99900547600101842
- Language
- English
- Resource Type
- Journal article