Frustrated Lewis pairs-assisted reduction of carbonyl compounds

Ales Marek; Martin Holst Friborg Pedersen

doi:10.1016/j.tet.2014.12.086

Frustrated Lewis pairs-assisted reduction of carbonyl compounds

Ales Marek, Martin Holst Friborg Pedersen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

An alternative and robust method for the reduction of carbonyl groups by frustrated Lewis pairs (FLPs) is reported in this paper. With its very mild reaction conditions, good to excellent yields, absolute regioselectivity and the non-metallic character of the reagent, it provides an excellent tool for H-1, H-2 as well as H-3 chemistry. It is a new strategy for the one-pot synthesis of aromatic alcohols selectively labeled with heavy isotopes of hydrogen. © 2015 Elsevier Ltd. All rights reserved.

Original language	English
Journal	Tetrahedron
Volume	71
Issue number	6
Pages (from-to)	917-921
Number of pages	5
ISSN	0040-4020
DOIs	https://doi.org/10.1016/j.tet.2014.12.086
Publication status	Published - 2015

Keywords

regioselectivity
aromatic alcohols
carbonyl compounds
deuterium gas
protium 1333-74-0
tris(pentafluorophenyl)borane-Lewis base metabolic-drug
tritium gas
10060, Biochemistry studies - General
12512, Pathology - Therapy
22002, Pharmacology - General
22003, Pharmacology - Drug metabolism and metabolic stimulators
deuterium labeling method laboratory techniques
one-pot synthesis laboratory techniques
Biochemistry and Molecular Biophysics
Methods and Techniques
Pharmacology
CHEMISTRY,
FREE CATALYTIC-HYDROGENATION
HETEROLYTIC DIHYDROGEN ACTIVATION
METAL-FREE
H-2 ACTIVATION
BORANE
REACTIVITY
MECHANISM
IMINES
B(C6F5)(3)
CLEAVAGE
Frustrated Lewis pairs
Hydrogen activation
Benzyl alcohol
Tritium labeling
Labeled compounds

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10.1016/j.tet.2014.12.086

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title = "Frustrated Lewis pairs-assisted reduction of carbonyl compounds",

abstract = "An alternative and robust method for the reduction of carbonyl groups by frustrated Lewis pairs (FLPs) is reported in this paper. With its very mild reaction conditions, good to excellent yields, absolute regioselectivity and the non-metallic character of the reagent, it provides an excellent tool for H-1, H-2 as well as H-3 chemistry. It is a new strategy for the one-pot synthesis of aromatic alcohols selectively labeled with heavy isotopes of hydrogen. {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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author = "Ales Marek and Pedersen, {Martin Holst Friborg}",

year = "2015",

doi = "10.1016/j.tet.2014.12.086",

language = "English",

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T1 - Frustrated Lewis pairs-assisted reduction of carbonyl compounds

AU - Marek, Ales

AU - Pedersen, Martin Holst Friborg

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AB - An alternative and robust method for the reduction of carbonyl groups by frustrated Lewis pairs (FLPs) is reported in this paper. With its very mild reaction conditions, good to excellent yields, absolute regioselectivity and the non-metallic character of the reagent, it provides an excellent tool for H-1, H-2 as well as H-3 chemistry. It is a new strategy for the one-pot synthesis of aromatic alcohols selectively labeled with heavy isotopes of hydrogen. © 2015 Elsevier Ltd. All rights reserved.

KW - regioselectivity

KW - aromatic alcohols

KW - carbonyl compounds

KW - deuterium gas

KW - protium 1333-74-0

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KW - tritium gas

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KW - Hydrogen activation

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DO - 10.1016/j.tet.2014.12.086

M3 - Journal article

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SP - 917

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JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

Frustrated Lewis pairs-assisted reduction of carbonyl compounds

Abstract

Keywords

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