Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH4

Alistair J. MacNair; [No Value] Ming-Ming Tran; Jennifer E. Nelson; G. Usherwood Sloan; Alan Ironmonger; Stephen P. Thomas

doi:10.1039/c4ob00945b

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH4

Alistair J. MacNair, [No Value] Ming-Ming Tran, Jennifer E. Nelson, G. Usherwood Sloan, Alan Ironmonger, Stephen P. Thomas^*

^*Corresponding author for this work

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

Abstract

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron (III) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH₄, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

Original language	English
Pages (from-to)	5082-5088
Journal	Organic & Biomolecular chemistry
Volume	12
Issue number	28
Early online date	23 May 2014
DOIs	https://doi.org/10.1039/c4ob00945b
Publication status	Published - 28 Jul 2014

Keywords / Materials (for Non-textual outputs)

LITHIUM ALUMINUM-HYDRIDE
AROMATIC NITRO-COMPOUNDS
SODIUM-BOROHYDRIDE
CHEMOSELECTIVE REDUCTION
SELECTIVE REDUCTION
UNACTIVATED ALKENES
RADICAL-ANION
NITROARENES
NITROBENZENE
ALKYNES

Access to Document

10.1039/c4ob00945b

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4
This an open access article published under a Creative Commons Attribution (CC-BY) 3.0 Unported Licence.
Final published version, 274 KBLicence: Creative Commons: Attribution (CC-BY)

http://pubs.rsc.org/en/content/articlehtml/2014/ob/c4ob00945b

Cite this

@article{ce75bf3bf42849aea86aea2032ec1682,

title = "Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH4",

abstract = "An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron (III) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.",

keywords = "LITHIUM ALUMINUM-HYDRIDE, AROMATIC NITRO-COMPOUNDS, SODIUM-BOROHYDRIDE, CHEMOSELECTIVE REDUCTION, SELECTIVE REDUCTION, UNACTIVATED ALKENES, RADICAL-ANION, NITROARENES, NITROBENZENE, ALKYNES",

author = "MacNair, {Alistair J.} and {Ming-Ming Tran}, {[No Value]} and Nelson, {Jennifer E.} and Sloan, {G. Usherwood} and Alan Ironmonger and Thomas, {Stephen P.}",

year = "2014",

month = jul,

day = "28",

doi = "10.1039/c4ob00945b",

language = "English",

volume = "12",

pages = "5082--5088",

journal = "Organic & Biomolecular chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "28",

}

TY - JOUR

T1 - Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH4

AU - MacNair, Alistair J.

AU - Ming-Ming Tran, [No Value]

AU - Nelson, Jennifer E.

AU - Sloan, G. Usherwood

AU - Ironmonger, Alan

AU - Thomas, Stephen P.

PY - 2014/7/28

Y1 - 2014/7/28

N2 - An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron (III) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

AB - An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron (III) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

KW - LITHIUM ALUMINUM-HYDRIDE

KW - AROMATIC NITRO-COMPOUNDS

KW - SODIUM-BOROHYDRIDE

KW - CHEMOSELECTIVE REDUCTION

KW - SELECTIVE REDUCTION

KW - UNACTIVATED ALKENES

KW - RADICAL-ANION

KW - NITROARENES

KW - NITROBENZENE

KW - ALKYNES

U2 - 10.1039/c4ob00945b

DO - 10.1039/c4ob00945b

M3 - Article

SN - 1477-0520

VL - 12

SP - 5082

EP - 5088

JO - Organic & Biomolecular chemistry

JF - Organic & Biomolecular chemistry

IS - 28

ER -

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH4

Abstract

Keywords / Materials (for Non-textual outputs)

Access to Document

Fingerprint

Cite this