Iron-Catalysed Reduction of Olefins using a Borohydride Reagent

Tom S. Carter; Lea Guiet; Dominik J. Frank; James West; Stephen P. Thomas

doi:10.1002/adsc.201200577

Iron-Catalysed Reduction of Olefins using a Borohydride Reagent

Tom S. Carter, Lea Guiet, Dominik J. Frank, James West, Stephen P. Thomas^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

20 Citations (Scopus)

Abstract

The iron-catalysed reduction of olefins has been achieved using a simple iron salt and sodium triethylborohydride. A wide range of mono- and trans-1,2-disubstituted alkenes have been reduced (91100%) using 25mol% iron(II) triflate, 1mol% N-methyl-2-pyrrolidinone and 4equivalents of sodium triethylborohydride. The reduction of alkynes to alkanes is also reported (up to 84%). Significantly, the reduction of trisubstituted alkenes has also been achieved (6086%).

Original language	English
Pages (from-to)	880-884
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	5
DOIs	https://doi.org/10.1002/adsc.201200577
Publication status	Published - Mar 2013

Keywords

catalysis
hydrogenation
iron
olefins
reduction
CROSS-COUPLING REACTIONS
ASYMMETRIC TRANSFER HYDROGENATION
GRIGNARD-REAGENTS
ARYL IODIDES
COMPLEXES
ALKENES
ALKYNES
ACETOPHENONE
HALIDES
FE

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Asymmetric Cross-Coupling via Iron-Catalysed Reductive Cross-Coupling
Thomas, S. P. (Principal Investigator)
9/01/12 → 9/01/13
Project: Research

Cite this

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title = "Iron-Catalysed Reduction of Olefins using a Borohydride Reagent",

abstract = "The iron-catalysed reduction of olefins has been achieved using a simple iron salt and sodium triethylborohydride. A wide range of mono- and trans-1,2-disubstituted alkenes have been reduced (91100%) using 25mol% iron(II) triflate, 1mol% N-methyl-2-pyrrolidinone and 4equivalents of sodium triethylborohydride. The reduction of alkynes to alkanes is also reported (up to 84%). Significantly, the reduction of trisubstituted alkenes has also been achieved (6086%).",

keywords = "catalysis, hydrogenation, iron, olefins, reduction, CROSS-COUPLING REACTIONS, ASYMMETRIC TRANSFER HYDROGENATION, GRIGNARD-REAGENTS, ARYL IODIDES, COMPLEXES, ALKENES, ALKYNES, ACETOPHENONE, HALIDES, FE",

author = "Carter, {Tom S.} and Lea Guiet and Frank, {Dominik J.} and James West and Thomas, {Stephen P.}",

year = "2013",

month = mar,

doi = "10.1002/adsc.201200577",

language = "English",

volume = "355",

pages = "880--884",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "5",

}

TY - JOUR

T1 - Iron-Catalysed Reduction of Olefins using a Borohydride Reagent

AU - Carter, Tom S.

AU - Guiet, Lea

AU - Frank, Dominik J.

AU - West, James

AU - Thomas, Stephen P.

PY - 2013/3

Y1 - 2013/3

N2 - The iron-catalysed reduction of olefins has been achieved using a simple iron salt and sodium triethylborohydride. A wide range of mono- and trans-1,2-disubstituted alkenes have been reduced (91100%) using 25mol% iron(II) triflate, 1mol% N-methyl-2-pyrrolidinone and 4equivalents of sodium triethylborohydride. The reduction of alkynes to alkanes is also reported (up to 84%). Significantly, the reduction of trisubstituted alkenes has also been achieved (6086%).

AB - The iron-catalysed reduction of olefins has been achieved using a simple iron salt and sodium triethylborohydride. A wide range of mono- and trans-1,2-disubstituted alkenes have been reduced (91100%) using 25mol% iron(II) triflate, 1mol% N-methyl-2-pyrrolidinone and 4equivalents of sodium triethylborohydride. The reduction of alkynes to alkanes is also reported (up to 84%). Significantly, the reduction of trisubstituted alkenes has also been achieved (6086%).

KW - catalysis

KW - hydrogenation

KW - iron

KW - olefins

KW - reduction

KW - CROSS-COUPLING REACTIONS

KW - ASYMMETRIC TRANSFER HYDROGENATION

KW - GRIGNARD-REAGENTS

KW - ARYL IODIDES

KW - COMPLEXES

KW - ALKENES

KW - ALKYNES

KW - ACETOPHENONE

KW - HALIDES

KW - FE

U2 - 10.1002/adsc.201200577

DO - 10.1002/adsc.201200577

M3 - Article (Academic Journal)

SN - 1615-4150

VL - 355

SP - 880

EP - 884

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 5

ER -

Iron-Catalysed Reduction of Olefins using a Borohydride Reagent

Abstract

Keywords

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Asymmetric Cross-Coupling via Iron-Catalysed Reductive Cross-Coupling

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